The Bet
by Karen Singer
Chapter 20 (Thursday – week 3 Part 2 of 5)
Mel handled several clients in her office, then had a mercifully short meeting with a judge before getting back to her office again – well before lunchtime. When she got there, 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 dropped 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 tired 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 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 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 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 need to pee hitting 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. Ok?” 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. “Ok, 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 out 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 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 again.
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 try all that 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 again just a bit. Ok?”
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, and he loved it. It was really sensual. As fantastic as Mel’s touch had been last night, Cassie was really much better. But then he felt her beginning to play around his asshole again and he waited breathless for her to really move her attention to it. Finally, her finger was there, pushing, then harder. He felt her finger go in. Why did he love it so much? He just did! 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 already. 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, feeling it getting wetter and wetter.
“That’s ok, baby,” she replied, still highly amused. “I guess we should have expected little accidents like that to happen.
He said nothing, but 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 all different circumstances that were really giving him the problems. His troubling thoughts were momentarily interrupted by the feeling of Cassie’s fingers shoving another suppository up inside of him again. And that was another problem, he realized. How do you fight the damn suppositories?
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.”
Tuesday, March 30, 2010
Friday, March 26, 2010
The Bet - Chapter 20 (Thursday – week 3 Part 1 of 5)
The Bet
by Karen Singer
Chapter 20 (Thursday – week 3 Part 1 of 5)
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 she realized that even in her dreams, 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. His diapers were over-loaded again, not just from wetting them, but from the damn suppository that Mel had stuck 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… he didn’t remember waking up at all for anything else. Not once. Yet his diapers 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 not once during either night did he remember wetting himself.
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 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. She had really loved the unintended consequences of his 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, ok, 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, and she had wound up ruining his ability to have an orgasm. She hadn’t meant to and she felt really bad about that – especially since she had promised him. Yet the fact that he couldn’t orgasm still held a fascination for her. What did she really want?
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? Ok, 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 knew 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. It felt like he had lost something again. It also felt a bit like when he had put the blouse on yesterday, 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 a strong feeling 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 better.
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 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 looking for a reply. But he couldn’t think of one 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 stood back by her sink 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 noticed 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 it 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. “I’m 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. “Ok, you’ve got a small point there, but it still looks dorky. Your makeup looks good today though. 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, thankful that it was all carpeted, 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 ok, 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 shook her head and rolled her eyes. It was time to change the subject. “Hey, so have you heard any feedback on our project yet?”
by Karen Singer
Chapter 20 (Thursday – week 3 Part 1 of 5)
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 she realized that even in her dreams, 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. His diapers were over-loaded again, not just from wetting them, but from the damn suppository that Mel had stuck 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… he didn’t remember waking up at all for anything else. Not once. Yet his diapers 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 not once during either night did he remember wetting himself.
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 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. She had really loved the unintended consequences of his 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, ok, 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, and she had wound up ruining his ability to have an orgasm. She hadn’t meant to and she felt really bad about that – especially since she had promised him. Yet the fact that he couldn’t orgasm still held a fascination for her. What did she really want?
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? Ok, 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 knew 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. It felt like he had lost something again. It also felt a bit like when he had put the blouse on yesterday, 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 a strong feeling 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 better.
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 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 looking for a reply. But he couldn’t think of one 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 stood back by her sink 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 noticed 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 it 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. “I’m 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. “Ok, you’ve got a small point there, but it still looks dorky. Your makeup looks good today though. 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, thankful that it was all carpeted, 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 ok, 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 shook her head and rolled her eyes. It was time to change the subject. “Hey, so have you heard any feedback on our project yet?”
Tuesday, March 23, 2010
The Bet - Chapter 19 (Wednesday – week 3 Part 5 of 5)
The Bet
by Karen Singer
Chapter 19 (Wednesday – week 3 Part 5 of 5)
When Mel came back, she helped him out of the tub and dried him off herself. Her attention was really nice. Sensual in a way. But Chad’s mind was more on what lay ahead and he wasn’t looking forward to it. “Come along now baby,” she said as she took him by the hand and led him into her bedroom.
The blankets on her bed were pulled back and the top was heavily protected under layers of plastic and very thick diapers. He could see the ropes attached to the headboard and the footboard. With a sigh of inevitability, he laid down on her bed and held his arms over his head so she could tie them. “Good baby,” she crooned softly. He hated it, but her voice sent a quick thrill through him.
All too soon, his arms were stretched tightly above him and his legs were stretched the opposite direction. He wasn’t going anywhere and he knew it. He didn’t even try. This time though, Mel climbed up on the bed and laid down next to him. She propped her head up on a pillow and watched him. He turned his head to look at her. She really was a beautiful woman. If only, if only!
Mel reached out and ran her hand lightly over his chest. Her touch sent instant thrills throughout him. “Cassie tells me that you did really well today when she tried to stimulate you.”
He was a bit surprised. “Yeah,” he admitted sheepishly. “I guess I did.”
“You’re learning really well already then.” He didn’t reply. She was right, he guessed he was learning… something. “She also said that you’re having some very interesting reactions when she plays with your backside. Is that right?”
He really didn’t want to admit it, but he had no doubt that Cassie had shown her the really embarrassing pictures from last night. The ones she had said she wasn’t going to show Mel. He blushed deeply and closed his eyes. The pictures meant that he couldn’t deny it. He hated saying it. “Yes, Mistress. I did.”
She was about to continue, but suddenly he was still speaking. His eyes were still closed as he spoke. “You saw the pictures from last night.”
She was taken off guard. What was he talking about? “Yes, I did see the pictures,” she replied, wondering what any of the pictures she had seen had to do with the present situation.
He opened his eyes finally and looked at her. “You saw how I reacted when they stuck that thing in me. I loved it. I hate that I did, but I loved it.” His voice was growing more and more upset and emotional. He began thrashing at his bonds in frustration. “I fucked myself on it!” he finally admitted as tears began falling from his eyes. He turned his head away from her as if trying to hide. “I hate myself for it, but I couldn’t help it,” he added a bit more softly.
Mel was shocked. Deeply shocked. Cassie hadn’t shown her any pictures like what he was describing. Obviously, Chad was very upset, and his anger was focused on himself and only himself. “Shhh, Sissy,” she said softly. “It’s alright. You don’t have to be angry about it.”
He turned his head back to face her. “But I am angry. I shouldn’t like it that much!” He turned his head away again.
Mel took a deep breath. She needed time to think, but now was not the time. There were other things to do first. “It’s ok, baby,” she said softly again. “Listen… Look at me.” She waited till he turned his head back again. “You’ve been wearing that chastity device for a whole week now. And you’ve done really well with it. I’m proud of you. So tonight, is not about me. Tonight is only about you. Tonight you’re going to get some reward.” She watched him as he took that in. It took a few seconds, but she suddenly saw his eyes widen in surprise.
“Reward? You mean it?”
She nodded her head. “Yes. You deserve it.”
“You’re going to grant me some relief?”
She giggled. “Definitely.” Then she put her mischievous smile on her face, “Eventually.”
She rolled off the bed and walked around to the other side where she sat down next to him. She looked at his chastity device. She needed to remove it. But there was something else starting to intrude into her mind. Cassie had said that she needed to explore his newfound interest. And he had just told her how much he had love it… while at the same time telling her how much he hated it. But she was curious. “Sissy,” she finally said softly, “would you mind very much if you showed me how you like your bottom played with?”
Chad’s mouth gaped open in disbelief. What was she asking? He began thrashing at his bonds and shaking his head back and forth again in frustration. Didn’t she understand how much he loathed himself because of it? But at the same time, he felt the powerful need from having no sexual relief in so long. And as he slowed his thrashing, that need became remembered feelings from doing it before. He wanted it. He needed it. But he hated it so much!
Mel watched him thrashing on her bed. As he finally slowed down again, she was about to say that it was fine, that he didn’t have to, but he beat her to it. “Ok… Yes, Mistress.” He said simply.
She was shocked. After all his thrashing about, he was suddenly agreeing? “Are you sure? We don’t have to…”
He closed his eyes. “Yes,” he said again in almost a whisper.
She moved down to the foot of the bed and untied his feet, then she released his arms. As he rubbed his wrists, she asked, “How should we do this?”
Chad covered his face in his hands as if to hide for a few moments. The he rolled over and pulled his legs up under him, exposing his naked backside up into the air for her. “Cassie massages me with baby lotion first,” he explained with his face stuck into her mattress and his arms covering his head. There was no way he could look at her. He was too ashamed.
“Ok,” she replied. His voice was a bit muffled by his position, but she wasn’t going to say anything about it. She quickly grabbed the baby lotion off of her nightstand and squirted it onto his backside. She saw him shudder at the sudden cold feeling. But she began massaging it into him, all around him. “What’s next?” she asked.
Chad surrendered himself to the wonderful sensation of Mel rubbing the baby lotion all over his backside. He heard her question, but he was too occupied with enjoyable sensations just then to answer. Without realizing it, he began moving his butt back and forth against the motions of her hands, increasing the pleasurable feelings. But he needed more. He wanted more. He had to tell her.
Mel could barely understand him when he spoke since he was speaking into the mattress. But she did her best to listen intently. “She usually starts to play with my hole just a little bit at a time. Then she slowly increases the pressure till her finger just slides in. Eventually, she works it back and forth. But as you saw from the pictures last night, they used something else on me instead.”
Mel lightly moved her finger over his little hole and pressed lightly. She saw the immediate reaction in his whole body. What pictures was he referring to? Obviously Cassie had some that she hadn’t shown her. And what had they used on him? She thought about what Cassie had suggested earlier. She had a vibrator of her own in her drawer and she had put fresh batteries in it just a little while ago, intending to use it on him at Cassie’s earlier request. Had Cassie and Sandy used something similar?
Instead of putting her finger up inside of him, she leaned down close to where he could hear her better. “Baby, I have a little toy we can try on you if you like. Can I?”
His muffled reply took a few moments. “Yes.” She thought she heard the sniffle of some tears. She hugged him briefly then opened her nightstand and pulled her vibrator out. He was still hunkered down, ass in the air, head into the mattress. “It’s ok, baby. It’s nothing to be ashamed of,” she told him softly. He turned his head away from her. Obviously to him it was.
“Come on,” she said softly. “Why don’t you pull your head up a bit. Besides, I want to see your little thingy all trapped inside of its cage while I do this.” He didn’t move. She leaned close to him again. “And then maybe I’ll take it off.”
He turned his head back towards her and moved his arm so he could look at her. “You mean it?”
“Of course.”
With a weary sigh, he hauled himself up onto his hands and knees on her bed. She smiled at him. “That’s better, baby.” Her words of praise sent thrills throughout him. She reached under him and lightly grabbed his chastity device and shook it lightly back and forth. “We’ll get this thing off of you in just a little bit.” She grabbed some KY jelly out of her drawer and lubed her vibrator well, then she set it lightly against his backside. “Ready?” she asked.
From his now kneeling position, he turned his head to look back at her. He was a bit frightened. This wasn’t at all like the sensual way that Cassie did it. He took a big breath to steady himself and nodded. “I guess so.” He turned his head away and closed his eyes. He didn’t want to look.
This was all new to Mel. What should she do? She was only guessing as she went along. Very lightly, she placed the tip of the vibrator against his hole. Did he want it turned on? She wasn’t sure so she decided to leave it off for a while. She pressed it harder against him. How hard would she have to press before it went in? What would happen when it went in? But as she held it there, trying to decide if she should push on it or not, she suddenly felt him pushing back against it a little bit. She pushed a bit harder towards him. Then a bit harder still. Her eyes went wide as the tip of it actually began to penetrate him. She saw his whole body tense up tightly beneath her.
The electric current shocked its way through him once again the moment her dildo penetrated him. Why did he like this so much? Why did it have to feel so damn good? The toy she was using on him wasn’t at all like whatever Cassie had used on him last night though. This one was smooth and skinnier, not fatter and ribbed. As the toy slowly slipped further and further into him, he realized that it gave him a lot less sensation since it was so totally smooth. Yet still, he loved it.
Mel kept pushing, watching wide eyed as the vibrator slowly disappeared up inside of him. How far did she have to push it? Would it hurt him if she pushed it too far? She worried about that. It was almost in up to her hand - as far as she would probably use it on herself when she felt him trying to move away from him. She pulled back on it now and watched as it came out again. But she didn’t remove it completely. Very soon, she was pushing on it as he was moving back towards her again. A minute later, she was grabbing it with both hands to hold it steady as he began rhythmically moving himself in and out against it.
Chad felt it going in and out of him. He was doing it now, not her. He was controlling it. He had to. He hated doing it, but he just had to – she wasn’t providing him with enough sensation. He began pumping himself against it harder, faster. But it wasn’t enough. He needed sexual relief… badly! Her little dido felt fantastic, but it wasn’t enough. Not by a long shot. He needed his penis uncovered… untrapped… where it could get hard. He needed to feel something from his penis to get off. He thought about peeing, but there was nothing ready to come out of him. Still, he pumped himself against her toy.
Mel held on harder as Chad rocked himself back and forth, obviously enthralled by what he was feeling. Did it feel anything like she felt when she used it on herself? Somehow she doubted that. She decided to try moving it around a bit. She rocked it back and forth as he pumped in and out, then she tried rocking it up and down.
Chad felt her moving the toy around now. The added sensation felt incredible. Much better than when she just held it still. But now she was pushing it up and down, over and over again, and something felt different, strange. It almost felt like he had to pee, but he didn’t have to pee. But then there was something coming out of his penis as if he were peeing. And it felt good, really good. But he needed more. He needed to touch himself. He needed to get hard to climax.
Mel stared in disbelief as she saw the liquid suddenly coming out of him. She thought he was peeing at first which really thrilled her. Imagine… peeing during sex - when before he couldn’t pee because he was sexually stimulated. But as she looked closer, she saw that the liquid that came out of him wasn’t pee at all, it was milky and thick. She glanced quickly under him. His penis, still trapped in the device, was completely small and tiny. No reaction from that at all, yet it was dripping cum as if he were peeing. She kept pumping the dildo up and down as he rocked even harder against it till the liquid stopped coming out of him.
Chad suddenly groaned in frustration and slapped the bed with his arms as he bent his head down into the mattress again. He stopped moving. It was no use. He couldn’t get any relief from just the anal stimulation – no matter how good if felt. He felt Mel pulling the toy away.
Mel put the vibrator back on her nightstand and put her arm over him. “Are you ok?” she asked tentatively.
It took a moment before he could collect himself enough to answer. “Yeah.” He got fully back up on his hands and knees again. I need more than that to get off though. I need to be able to get hard. Please, Mistress?” he asked pleadingly. “I really need it.”
She smiled at him. “Of course. But let me do it for you.” She had been fascinated by what she had just witnessed – taken part in. Cassie had been right, it was just something that she had never considered. And judging by Chad’s reactions, it was something new in his life as well. She laughed a bit as she pulled on the diaper underneath him that had collected all his sperm. “You made a mess though,” she said as he moved his weight off of it so she could remove it.
She rolled him over on his back and grabbed his wrist and pulled it up toward her headboard. He rolled his eyes at her and looked pleadingly at her, not wanting her to tie him up again. “Shhh,” she said softly. “I want to do this for you, ok?”
He reluctantly agreed and soon he was once again completely bound and helpless on her bed. She was fiddling with the chastity device now, removing the lock and placing it on her nightstand. He held his breath as she pulled the encasing cover off of him. The cold air that hit his shriveled penis felt good. He wanted badly to touch it… to massage it, yet he couldn’t because she had him tied. She removed the rest of the device, the part that held it all so firmly attached to him. He breathed a sigh of relief as it was gone. Again he wanted to touch himself, or at least to scratch at the area where it had been removed from. “I’ll be right back, baby,” she said softly. Then she was gone.
She came back a minute later with her razor and a washcloth. Very shortly, she had removed all the stray hairs from that area of him and was massaging his now free cock with her warm wet washcloth. It felt like heaven. He closed his eyes and concentrated on it. His sexual need was so great. She was touching him, massaging him. Yet he wasn’t getting hard. As if he couldn’t get hard.
Mel looked at him strangely as she used the washcloth on him. She was massaging him with the washcloth and he appeared to be loving it, yet his penis wasn’t reacting. She put the washcloth down and began using just her fingers instead, touching him, urging him with her hands to get hard in the way that she had totally denied him before. It took a while, but eventually he swelled somewhat in her hands. But it was only somewhat. She felt him trying to rock back and forth, pushing against her hands, and she did everything she could but he wouldn’t get any harder. He couldn’t seem to come any closer to the relief that she knew he needed… and that she wanted him to have. She was becoming frustrated from the effort, and obviously, so was he.
Chad tried as hard as he could. Her hands were like magic, but he wasn’t getting any harder, and he couldn’t seem to cum. It hit him fully then. She had inadvertently milked him. Or maybe it wasn’t so inadvertently… he didn’t know. But either way, he wouldn’t be able to get any relief. Not for quite a while. He groaned in frustration as he thrashed against his bonds.
“What’s wrong, baby,” she asked, totally concerned.
“You milked me!” he almost shouted.
“I what?”
“You got all the cum out of me already and didn’t allow me to get the full release that I need. I can’t come now!”
His frustration was so evident. Milked him? She had to think about that. It was a concept she had just barely heard of. Was that what had happened when he had released all that sperm earlier? And now he couldn’t cum? Was it true? That wasn’t what she had intended at all!
“You’re kidding!” she exclaimed. “You mean you can’t cum now?”
“No! There’s nothing left. Just all this pent up insatiable need! And it’s so frustrating!”
Mel was actually crestfallen for him. She placed her hand lovingly on his chest. “I’m sorry, baby. I didn’t mean to. I didn’t know. So you mean there’s no way?”
He shook his head. “Believe me, I’d really love to. I need to… but I can’t.”
She sighed. “I’m sorry, baby,” she repeated.
He didn’t know whether he believed her or not. Once again he was being denied - even if she hadn’t meant to do it to him. His frustration suddenly increased all the more as he felt her rubbing some kind of lotion all over his privates then fastening the chastity device back on again. He almost screamed as she placed the main cover back over his penis once again. Trapping him. Denying him. Totally.
And when she stuck the suppository up inside of him, he received no pleasure from the act at all, only revulsion. With almost clinical quickness, she was fastening up the thick night diapers all around him.
His life was back to the usual again. The relief had been offered… then taken away. Denied.
by Karen Singer
Chapter 19 (Wednesday – week 3 Part 5 of 5)
When Mel came back, she helped him out of the tub and dried him off herself. Her attention was really nice. Sensual in a way. But Chad’s mind was more on what lay ahead and he wasn’t looking forward to it. “Come along now baby,” she said as she took him by the hand and led him into her bedroom.
The blankets on her bed were pulled back and the top was heavily protected under layers of plastic and very thick diapers. He could see the ropes attached to the headboard and the footboard. With a sigh of inevitability, he laid down on her bed and held his arms over his head so she could tie them. “Good baby,” she crooned softly. He hated it, but her voice sent a quick thrill through him.
All too soon, his arms were stretched tightly above him and his legs were stretched the opposite direction. He wasn’t going anywhere and he knew it. He didn’t even try. This time though, Mel climbed up on the bed and laid down next to him. She propped her head up on a pillow and watched him. He turned his head to look at her. She really was a beautiful woman. If only, if only!
Mel reached out and ran her hand lightly over his chest. Her touch sent instant thrills throughout him. “Cassie tells me that you did really well today when she tried to stimulate you.”
He was a bit surprised. “Yeah,” he admitted sheepishly. “I guess I did.”
“You’re learning really well already then.” He didn’t reply. She was right, he guessed he was learning… something. “She also said that you’re having some very interesting reactions when she plays with your backside. Is that right?”
He really didn’t want to admit it, but he had no doubt that Cassie had shown her the really embarrassing pictures from last night. The ones she had said she wasn’t going to show Mel. He blushed deeply and closed his eyes. The pictures meant that he couldn’t deny it. He hated saying it. “Yes, Mistress. I did.”
She was about to continue, but suddenly he was still speaking. His eyes were still closed as he spoke. “You saw the pictures from last night.”
She was taken off guard. What was he talking about? “Yes, I did see the pictures,” she replied, wondering what any of the pictures she had seen had to do with the present situation.
He opened his eyes finally and looked at her. “You saw how I reacted when they stuck that thing in me. I loved it. I hate that I did, but I loved it.” His voice was growing more and more upset and emotional. He began thrashing at his bonds in frustration. “I fucked myself on it!” he finally admitted as tears began falling from his eyes. He turned his head away from her as if trying to hide. “I hate myself for it, but I couldn’t help it,” he added a bit more softly.
Mel was shocked. Deeply shocked. Cassie hadn’t shown her any pictures like what he was describing. Obviously, Chad was very upset, and his anger was focused on himself and only himself. “Shhh, Sissy,” she said softly. “It’s alright. You don’t have to be angry about it.”
He turned his head back to face her. “But I am angry. I shouldn’t like it that much!” He turned his head away again.
Mel took a deep breath. She needed time to think, but now was not the time. There were other things to do first. “It’s ok, baby,” she said softly again. “Listen… Look at me.” She waited till he turned his head back again. “You’ve been wearing that chastity device for a whole week now. And you’ve done really well with it. I’m proud of you. So tonight, is not about me. Tonight is only about you. Tonight you’re going to get some reward.” She watched him as he took that in. It took a few seconds, but she suddenly saw his eyes widen in surprise.
“Reward? You mean it?”
She nodded her head. “Yes. You deserve it.”
“You’re going to grant me some relief?”
She giggled. “Definitely.” Then she put her mischievous smile on her face, “Eventually.”
She rolled off the bed and walked around to the other side where she sat down next to him. She looked at his chastity device. She needed to remove it. But there was something else starting to intrude into her mind. Cassie had said that she needed to explore his newfound interest. And he had just told her how much he had love it… while at the same time telling her how much he hated it. But she was curious. “Sissy,” she finally said softly, “would you mind very much if you showed me how you like your bottom played with?”
Chad’s mouth gaped open in disbelief. What was she asking? He began thrashing at his bonds and shaking his head back and forth again in frustration. Didn’t she understand how much he loathed himself because of it? But at the same time, he felt the powerful need from having no sexual relief in so long. And as he slowed his thrashing, that need became remembered feelings from doing it before. He wanted it. He needed it. But he hated it so much!
Mel watched him thrashing on her bed. As he finally slowed down again, she was about to say that it was fine, that he didn’t have to, but he beat her to it. “Ok… Yes, Mistress.” He said simply.
She was shocked. After all his thrashing about, he was suddenly agreeing? “Are you sure? We don’t have to…”
He closed his eyes. “Yes,” he said again in almost a whisper.
She moved down to the foot of the bed and untied his feet, then she released his arms. As he rubbed his wrists, she asked, “How should we do this?”
Chad covered his face in his hands as if to hide for a few moments. The he rolled over and pulled his legs up under him, exposing his naked backside up into the air for her. “Cassie massages me with baby lotion first,” he explained with his face stuck into her mattress and his arms covering his head. There was no way he could look at her. He was too ashamed.
“Ok,” she replied. His voice was a bit muffled by his position, but she wasn’t going to say anything about it. She quickly grabbed the baby lotion off of her nightstand and squirted it onto his backside. She saw him shudder at the sudden cold feeling. But she began massaging it into him, all around him. “What’s next?” she asked.
Chad surrendered himself to the wonderful sensation of Mel rubbing the baby lotion all over his backside. He heard her question, but he was too occupied with enjoyable sensations just then to answer. Without realizing it, he began moving his butt back and forth against the motions of her hands, increasing the pleasurable feelings. But he needed more. He wanted more. He had to tell her.
Mel could barely understand him when he spoke since he was speaking into the mattress. But she did her best to listen intently. “She usually starts to play with my hole just a little bit at a time. Then she slowly increases the pressure till her finger just slides in. Eventually, she works it back and forth. But as you saw from the pictures last night, they used something else on me instead.”
Mel lightly moved her finger over his little hole and pressed lightly. She saw the immediate reaction in his whole body. What pictures was he referring to? Obviously Cassie had some that she hadn’t shown her. And what had they used on him? She thought about what Cassie had suggested earlier. She had a vibrator of her own in her drawer and she had put fresh batteries in it just a little while ago, intending to use it on him at Cassie’s earlier request. Had Cassie and Sandy used something similar?
Instead of putting her finger up inside of him, she leaned down close to where he could hear her better. “Baby, I have a little toy we can try on you if you like. Can I?”
His muffled reply took a few moments. “Yes.” She thought she heard the sniffle of some tears. She hugged him briefly then opened her nightstand and pulled her vibrator out. He was still hunkered down, ass in the air, head into the mattress. “It’s ok, baby. It’s nothing to be ashamed of,” she told him softly. He turned his head away from her. Obviously to him it was.
“Come on,” she said softly. “Why don’t you pull your head up a bit. Besides, I want to see your little thingy all trapped inside of its cage while I do this.” He didn’t move. She leaned close to him again. “And then maybe I’ll take it off.”
He turned his head back towards her and moved his arm so he could look at her. “You mean it?”
“Of course.”
With a weary sigh, he hauled himself up onto his hands and knees on her bed. She smiled at him. “That’s better, baby.” Her words of praise sent thrills throughout him. She reached under him and lightly grabbed his chastity device and shook it lightly back and forth. “We’ll get this thing off of you in just a little bit.” She grabbed some KY jelly out of her drawer and lubed her vibrator well, then she set it lightly against his backside. “Ready?” she asked.
From his now kneeling position, he turned his head to look back at her. He was a bit frightened. This wasn’t at all like the sensual way that Cassie did it. He took a big breath to steady himself and nodded. “I guess so.” He turned his head away and closed his eyes. He didn’t want to look.
This was all new to Mel. What should she do? She was only guessing as she went along. Very lightly, she placed the tip of the vibrator against his hole. Did he want it turned on? She wasn’t sure so she decided to leave it off for a while. She pressed it harder against him. How hard would she have to press before it went in? What would happen when it went in? But as she held it there, trying to decide if she should push on it or not, she suddenly felt him pushing back against it a little bit. She pushed a bit harder towards him. Then a bit harder still. Her eyes went wide as the tip of it actually began to penetrate him. She saw his whole body tense up tightly beneath her.
The electric current shocked its way through him once again the moment her dildo penetrated him. Why did he like this so much? Why did it have to feel so damn good? The toy she was using on him wasn’t at all like whatever Cassie had used on him last night though. This one was smooth and skinnier, not fatter and ribbed. As the toy slowly slipped further and further into him, he realized that it gave him a lot less sensation since it was so totally smooth. Yet still, he loved it.
Mel kept pushing, watching wide eyed as the vibrator slowly disappeared up inside of him. How far did she have to push it? Would it hurt him if she pushed it too far? She worried about that. It was almost in up to her hand - as far as she would probably use it on herself when she felt him trying to move away from him. She pulled back on it now and watched as it came out again. But she didn’t remove it completely. Very soon, she was pushing on it as he was moving back towards her again. A minute later, she was grabbing it with both hands to hold it steady as he began rhythmically moving himself in and out against it.
Chad felt it going in and out of him. He was doing it now, not her. He was controlling it. He had to. He hated doing it, but he just had to – she wasn’t providing him with enough sensation. He began pumping himself against it harder, faster. But it wasn’t enough. He needed sexual relief… badly! Her little dido felt fantastic, but it wasn’t enough. Not by a long shot. He needed his penis uncovered… untrapped… where it could get hard. He needed to feel something from his penis to get off. He thought about peeing, but there was nothing ready to come out of him. Still, he pumped himself against her toy.
Mel held on harder as Chad rocked himself back and forth, obviously enthralled by what he was feeling. Did it feel anything like she felt when she used it on herself? Somehow she doubted that. She decided to try moving it around a bit. She rocked it back and forth as he pumped in and out, then she tried rocking it up and down.
Chad felt her moving the toy around now. The added sensation felt incredible. Much better than when she just held it still. But now she was pushing it up and down, over and over again, and something felt different, strange. It almost felt like he had to pee, but he didn’t have to pee. But then there was something coming out of his penis as if he were peeing. And it felt good, really good. But he needed more. He needed to touch himself. He needed to get hard to climax.
Mel stared in disbelief as she saw the liquid suddenly coming out of him. She thought he was peeing at first which really thrilled her. Imagine… peeing during sex - when before he couldn’t pee because he was sexually stimulated. But as she looked closer, she saw that the liquid that came out of him wasn’t pee at all, it was milky and thick. She glanced quickly under him. His penis, still trapped in the device, was completely small and tiny. No reaction from that at all, yet it was dripping cum as if he were peeing. She kept pumping the dildo up and down as he rocked even harder against it till the liquid stopped coming out of him.
Chad suddenly groaned in frustration and slapped the bed with his arms as he bent his head down into the mattress again. He stopped moving. It was no use. He couldn’t get any relief from just the anal stimulation – no matter how good if felt. He felt Mel pulling the toy away.
Mel put the vibrator back on her nightstand and put her arm over him. “Are you ok?” she asked tentatively.
It took a moment before he could collect himself enough to answer. “Yeah.” He got fully back up on his hands and knees again. I need more than that to get off though. I need to be able to get hard. Please, Mistress?” he asked pleadingly. “I really need it.”
She smiled at him. “Of course. But let me do it for you.” She had been fascinated by what she had just witnessed – taken part in. Cassie had been right, it was just something that she had never considered. And judging by Chad’s reactions, it was something new in his life as well. She laughed a bit as she pulled on the diaper underneath him that had collected all his sperm. “You made a mess though,” she said as he moved his weight off of it so she could remove it.
She rolled him over on his back and grabbed his wrist and pulled it up toward her headboard. He rolled his eyes at her and looked pleadingly at her, not wanting her to tie him up again. “Shhh,” she said softly. “I want to do this for you, ok?”
He reluctantly agreed and soon he was once again completely bound and helpless on her bed. She was fiddling with the chastity device now, removing the lock and placing it on her nightstand. He held his breath as she pulled the encasing cover off of him. The cold air that hit his shriveled penis felt good. He wanted badly to touch it… to massage it, yet he couldn’t because she had him tied. She removed the rest of the device, the part that held it all so firmly attached to him. He breathed a sigh of relief as it was gone. Again he wanted to touch himself, or at least to scratch at the area where it had been removed from. “I’ll be right back, baby,” she said softly. Then she was gone.
She came back a minute later with her razor and a washcloth. Very shortly, she had removed all the stray hairs from that area of him and was massaging his now free cock with her warm wet washcloth. It felt like heaven. He closed his eyes and concentrated on it. His sexual need was so great. She was touching him, massaging him. Yet he wasn’t getting hard. As if he couldn’t get hard.
Mel looked at him strangely as she used the washcloth on him. She was massaging him with the washcloth and he appeared to be loving it, yet his penis wasn’t reacting. She put the washcloth down and began using just her fingers instead, touching him, urging him with her hands to get hard in the way that she had totally denied him before. It took a while, but eventually he swelled somewhat in her hands. But it was only somewhat. She felt him trying to rock back and forth, pushing against her hands, and she did everything she could but he wouldn’t get any harder. He couldn’t seem to come any closer to the relief that she knew he needed… and that she wanted him to have. She was becoming frustrated from the effort, and obviously, so was he.
Chad tried as hard as he could. Her hands were like magic, but he wasn’t getting any harder, and he couldn’t seem to cum. It hit him fully then. She had inadvertently milked him. Or maybe it wasn’t so inadvertently… he didn’t know. But either way, he wouldn’t be able to get any relief. Not for quite a while. He groaned in frustration as he thrashed against his bonds.
“What’s wrong, baby,” she asked, totally concerned.
“You milked me!” he almost shouted.
“I what?”
“You got all the cum out of me already and didn’t allow me to get the full release that I need. I can’t come now!”
His frustration was so evident. Milked him? She had to think about that. It was a concept she had just barely heard of. Was that what had happened when he had released all that sperm earlier? And now he couldn’t cum? Was it true? That wasn’t what she had intended at all!
“You’re kidding!” she exclaimed. “You mean you can’t cum now?”
“No! There’s nothing left. Just all this pent up insatiable need! And it’s so frustrating!”
Mel was actually crestfallen for him. She placed her hand lovingly on his chest. “I’m sorry, baby. I didn’t mean to. I didn’t know. So you mean there’s no way?”
He shook his head. “Believe me, I’d really love to. I need to… but I can’t.”
She sighed. “I’m sorry, baby,” she repeated.
He didn’t know whether he believed her or not. Once again he was being denied - even if she hadn’t meant to do it to him. His frustration suddenly increased all the more as he felt her rubbing some kind of lotion all over his privates then fastening the chastity device back on again. He almost screamed as she placed the main cover back over his penis once again. Trapping him. Denying him. Totally.
And when she stuck the suppository up inside of him, he received no pleasure from the act at all, only revulsion. With almost clinical quickness, she was fastening up the thick night diapers all around him.
His life was back to the usual again. The relief had been offered… then taken away. Denied.
Friday, March 19, 2010
The Bet - Chapter 19 (Wednesday – week 3 Part 4 of 5)
The Bet
by Karen Singer
Chapter 19 (Wednesday – week 3 Part 4 of 5)
Chad cleaned up the kitchen while Sandy and Cassie went back to their apartment and Mel booted up her computer. The three women were having a good time, again, while he was being ignored and doing the maid’s work. His lot in life. But he hadn’t even had any dinner. Would he get anything to eat tonight? Probably a bunch of baby bottles of Mel’s lousy tea mixture before bed and that would be it!
Cassie and Sandy were back only minutes later. Sandy had a plastic bag in her hands. She opened it and let Mel see inside.
Mel walked into the kitchen and started playing with the highchair, trying to figure out how the top came off of it. It didn’t take her long. “Ok, Sissy, dinner time. Hop up here.”
Chad wasn’t at all happy about having to sit in the chair. Once in it, he couldn’t get out unless someone let him out. But he had no choice in the matter so he slowly, really more cautiously, approached the chair and climbed up into it. Sandy brought the seatbelts around him and fastened the ends together. Then Mel snapped the table top down and pushed it tightly into place against him. He was trapped into the darn thing again. He wiggled a bit trying to get his arms free, but as before, it was useless.
Mel watched Chad struggling briefly in the chair with a cruel smile on her face. But she surprised him then by pulling the table top off again. “Raise your arms,” she said as she held the top away from him. He quickly and gladly complied. Then she put the top back in place again. Chad was a lot happier. He squirmed around a bit and soon realized he was still stuck in the chair, but he was a lot happier now with his arms free.
Sandy pulled something out of the bag she was holding and handed it to Mel. Chad was aghast to see the bib Sandy had put on him last night. All too soon Mel had fastened it around his neck. “He really needs this,” Mel stated. “You should see how messy he gets when he eats his cereal in the morning.”
Sandy laughed, “I can imagine.” She then pulled out the divided plate that she had used last night from her bag and set it on the counter.
Mel walked over to take a better look at it while Sandy began pulling jar after jar of baby food out of her bag too. “Ohhh. Very pretty,” she remarked teasingly.
“Isn’t it?” Sandy replied with a laugh. She then started opening jars and with a teaspoon, emptying them onto the divided dish. When she was done, she proudly set the spoon on the dish and handed it to Mel. “All set,” she declared.
Mel grabbed it and looked at it for a moment. “I don’t think so,” she replied. Then she set the plate back down on the counter. Chad breathed a sigh of relief. But it was a short relief. “Wrong spoon,” Mel declared. Then she went into one of her drawers and pulled out one of the baby spoons that Chad had to use every morning with his cereal. All three women burst into fits of laughter while Chad sat in his chair and felt even more pangs of humiliation. Unfortunately, his humiliation was fueling his overly developed sexual need all too much and he began to feel the stings of pain from his chastity device.
All too soon, Mel sat the plate of baby food down in front of Chad along with one of her bottles of tea and he was forced to pick up the baby spoon and begin eating. And within moments, the first of the food had dripped off of his spoon and down his chin and onto his bib. Just great!
“See,” Mel declared, “I told you he was a messy eater.”
Chad had to sit and eat the whole plate of baby food while all three women left him alone and went out to Mel’s computer where she downloaded the pictures from Cassie. He heard them laughing as they looked through them all. Did Cassie include the really embarrassing ones? He had no way of knowing. He hoped not, but he wouldn’t put it past her. He could really only assume that she did.
The women were still laughing and looking at pictures as he was finishing his meal. They weren’t paying any attention to him. He decided to do some exploratory checking. He put his spoon down and reached out to the sides of the tray to see if he could remove it. He felt the release mechanism under the tray with both hands. He carefully pushed in on both sides at the same time and the tray in front of him suddenly moved slightly away from him. The sudden movement startled him and he quickly pulled his hands away and picked up his spoon again to keep eating. He glanced over at the women, they hadn’t noticed. Breathing a sigh of relief, he finished the only dinner he knew he was going to get. If he had to, he could get out of the chair by himself – as long as his arms were free!
Chad finished his dinner and his bottle, but the women were still laughing over the pictures – or whatever else they were looking at on Mel’s computer. He really had no idea. But now he was finished eating and he was still stuck in the chair. In a way, it was a bit like being stuck in the corner. But at least he was sitting down and he could move a little bit. He also had more to look at than two blank walls that were all too close to his eyes. But sitting stuck in the chair was still boring. He felt the need to pee again and let it out – reveling in how good it felt.
He was still sitting there, mostly forgotten, when Mel suddenly ushered Cassie and Sandy out. Mel came back to the kitchen and sat in one of the kitchen chairs near him. “You’re a mess,” she declared teasingly. “Just like a baby.”
He blushed. “Can I get up now?” he asked.
“When I’m ready,” she replied. She leaned her arm on the table and her head in her hand. “Dinner was good tonight,” she replied, “again. But I shouldn’t have to tell you that.”
He actually felt a wave of relief. “Thank you, Mistress. It means a lot to me to hear you say that. I was hoping to see how good it was myself though.”
“Maybe next time, Sissy.” She sat and stared at him. He wondered why.
“Cassie did a nice job on your hair last night.”
He wasn’t sure how to answer. He really wasn’t all that happy with what she had done to him – actually with several things she had done to him. “Did she?” he finally said.
Mel nodded. “It looked a lot better in the pictures through.”
He felt himself starting to blush a little bit. “I thought it looked way too feminine,” he admitted softly.
Mel smiled. “Perfect for you then. She said she used a curling iron on it last night. We’ll get you one tomorrow then Cassie can teach you how to use it.”
Chad looked at her horrified. He didn’t know how to answer. His entire life now was one humiliation piled on top of another!
“I heard you added some more makeup after you got to work today,” Mel continued when he didn’t say anything.
He blushed briefly again, then got worried. “I’m sorry, Mistress. I didn’t know you wouldn’t want me to.”
“I did want you to. I was very pleased to hear it.”
“Oh… Thank you,” he replied. Why would she say that?
“What made you decide to add the lipstick?”
He shrugged as best he could in his confining seat. “Robin suggested it. She said I looked too pale without it.”
The mention of Robin instantly sent a tiny bolt of annoyance through Mel’s body. The Robin woman again! She was starting to dislike her even more. There was no real reason for it, she just did. Was she pretty? Did Chad have a thing for her? She didn’t know. But obviously, this Robin had a lot of influence over him. Influence she was jealous of. Annoyed over Robin, Mel got up and released him from the confining highchair. “Finish cleaning up the kitchen now,” she ordered.
While Chad got busy cleaning up after dinner again, Mel walked into her bedroom to start preparing for later. She saw his uniform dress hanging on her closet door. She shook her head. As much as she would like seeing him in it tonight, it wasn’t going to happen. Not tonight at least. Tonight was about other things.
She went back out to the kitchen. “Stop what you’re doing for a few minutes.”
Chad turned the water off at the sink and looked at her questioningly.
“Go take your uniform home again and leave it there. Bring back one of your onesies instead.
Chad blinked. Take his uniform home? Why now? But he dutifully dropped into a quick curtsey and said “Yes, Mistress.” He quickly got his uniform and took it home and hung it in his closet. Then he found one of the onesies that she liked to lock him into. She hadn’t put him into one of them in quite a while. Why now? A few minutes later, he was back at her apartment again.
Mel took the onesie from Chad and held it up. She smiled at the sight of the babyish looking garment. “Get undressed. Just diapers and plastic panties.” Chad quickly complied and all too soon, Mel was helping fasten him into the babyish onesie. Fortunately, she didn’t add the lock. “Put your clothes in my clothes hamper,” she instructed him.
Chad did as he was told, but doing so reminded him of something. “Mistress, can I please do my laundry tonight? I’m running out of clothes.”
“Maybe later,” Mel replied. We have other things to do tonight. But right now, I want you to finish in the kitchen.
Chad went back to the kitchen. What did she have planned for tonight? He really had no idea. When the kitchen was done, Mel made him sit on the floor and drink another baby bottle of her tea. Chad wasn’t too happy about that. He suddenly had visions of her timing him again to see how soon he could pee.
But after he finished the bottle, Mel had him get started on the laundry and never once mentioned the timer. “Do all of my things first,” Mel instructed him as he began sorting through the clothes. “Don’t even think about doing any of your laundry till all of mine is done.”
Chad watched as Mel went back to her living room and picked up her laptop computer to keep working. He was relieved in several ways - no timing him to see how quickly he could pee, and more importantly, he really did need to get some laundry done.
Mel glanced at him occasionally as he worked around her apartment. Without being told, he cleaned her bathroom and dusted some furniture while the washer and dryer were running. Once in a while she got up to check his progress on the laundry. As she had instructed him, all of his things were still waiting to be cleaned. She watched the clock as he worked too. It was starting to get a bit later.
Just before he was about to start on his own laundry, she stopped him. “Put the laundry basket back into the bathroom now. It’s getting late and we have other things to do.”
Again Chad wondered what she had in mind, but his own laundry wasn’t even started yet. “But Mistress, can I at least get one load of my things into the washer first?”
“No, Sissy. It’s time for other things now.”
Again Chad had to wonder what she had in mind. Without realizing it, he was mentally bracing himself for more humiliation.
As Chad was carrying his dirty clothes back into her bathroom, she called after him. “Start the bathwater while you’re in there.”
As Chad turned the water on in the tub, he realized that she was going to be tying him up again and using him for her own little pleasures again. Ugh! He hated it, but he also loved it. What he hated was that she used him so hard and he was incapable of getting any relief. But why would she want him to run the bath water first? That was odd. Her bath usually came after she had abused him.
Mel walked into the bathroom with him. She watched as he poured some of the bath beads into the water. He glanced at her, questioning if he had put enough in. “A little bit more,” she told him with a smile.
As the tub was still filling, she unfastened his onesie and helped him out of it. Then she removed his plastic panties.
Chas was surprised when she removed his plastic panties. Was the bath for him instead?
“Lay down on the floor so I can remove your diapers,” she said. Chad felt a thrill of elation. It seemed that she wasn’t going to abuse him tonight. And a bath would really feel nice. As Mel was about to remove his diapers though, he suddenly realized that he had to pee slightly. He quickly stopped Mel from removing his diaper. “You might want to wait a moment on that,” he said, “I’m wetting myself right now.”
Mel smiled broadly at him. “Go right ahead,” she said sounding very satisfied.
After Mel had finally removed his diapers, Chad’s elation rose a whole lot more as Mel had him step into the warm scented bathwater. He laid back and allowed himself to relax and breathe in deeply. It felt so good!
Mel handed him her body sponge and he began cleaning himself off. The bath felt like a distinct pleasure. The only part he wasn’t crazy about was when Mel produced her razor and began removing the stray hairs from his body, making him totally smooth once again. “This is a lot easier now, since you’re shaving your own legs,” she commented. “From now on, make that part of your morning routine. I’m not going to mention it again.”
Chad felt a moment of bother about it, but it was no use resisting. “Yes, Mistress,” he replied.
“Lay back now and soak for a bit while I get the bedroom ready.”
Chad now knew exactly what to expect. She was going to tie him to her bed and probably torture him. He wasn’t looking forward to it. He concentrated instead on enjoying the pleasurable sensation of the warm bath while he still could - the one bright spot in his entire day.
by Karen Singer
Chapter 19 (Wednesday – week 3 Part 4 of 5)
Chad cleaned up the kitchen while Sandy and Cassie went back to their apartment and Mel booted up her computer. The three women were having a good time, again, while he was being ignored and doing the maid’s work. His lot in life. But he hadn’t even had any dinner. Would he get anything to eat tonight? Probably a bunch of baby bottles of Mel’s lousy tea mixture before bed and that would be it!
Cassie and Sandy were back only minutes later. Sandy had a plastic bag in her hands. She opened it and let Mel see inside.
Mel walked into the kitchen and started playing with the highchair, trying to figure out how the top came off of it. It didn’t take her long. “Ok, Sissy, dinner time. Hop up here.”
Chad wasn’t at all happy about having to sit in the chair. Once in it, he couldn’t get out unless someone let him out. But he had no choice in the matter so he slowly, really more cautiously, approached the chair and climbed up into it. Sandy brought the seatbelts around him and fastened the ends together. Then Mel snapped the table top down and pushed it tightly into place against him. He was trapped into the darn thing again. He wiggled a bit trying to get his arms free, but as before, it was useless.
Mel watched Chad struggling briefly in the chair with a cruel smile on her face. But she surprised him then by pulling the table top off again. “Raise your arms,” she said as she held the top away from him. He quickly and gladly complied. Then she put the top back in place again. Chad was a lot happier. He squirmed around a bit and soon realized he was still stuck in the chair, but he was a lot happier now with his arms free.
Sandy pulled something out of the bag she was holding and handed it to Mel. Chad was aghast to see the bib Sandy had put on him last night. All too soon Mel had fastened it around his neck. “He really needs this,” Mel stated. “You should see how messy he gets when he eats his cereal in the morning.”
Sandy laughed, “I can imagine.” She then pulled out the divided plate that she had used last night from her bag and set it on the counter.
Mel walked over to take a better look at it while Sandy began pulling jar after jar of baby food out of her bag too. “Ohhh. Very pretty,” she remarked teasingly.
“Isn’t it?” Sandy replied with a laugh. She then started opening jars and with a teaspoon, emptying them onto the divided dish. When she was done, she proudly set the spoon on the dish and handed it to Mel. “All set,” she declared.
Mel grabbed it and looked at it for a moment. “I don’t think so,” she replied. Then she set the plate back down on the counter. Chad breathed a sigh of relief. But it was a short relief. “Wrong spoon,” Mel declared. Then she went into one of her drawers and pulled out one of the baby spoons that Chad had to use every morning with his cereal. All three women burst into fits of laughter while Chad sat in his chair and felt even more pangs of humiliation. Unfortunately, his humiliation was fueling his overly developed sexual need all too much and he began to feel the stings of pain from his chastity device.
All too soon, Mel sat the plate of baby food down in front of Chad along with one of her bottles of tea and he was forced to pick up the baby spoon and begin eating. And within moments, the first of the food had dripped off of his spoon and down his chin and onto his bib. Just great!
“See,” Mel declared, “I told you he was a messy eater.”
Chad had to sit and eat the whole plate of baby food while all three women left him alone and went out to Mel’s computer where she downloaded the pictures from Cassie. He heard them laughing as they looked through them all. Did Cassie include the really embarrassing ones? He had no way of knowing. He hoped not, but he wouldn’t put it past her. He could really only assume that she did.
The women were still laughing and looking at pictures as he was finishing his meal. They weren’t paying any attention to him. He decided to do some exploratory checking. He put his spoon down and reached out to the sides of the tray to see if he could remove it. He felt the release mechanism under the tray with both hands. He carefully pushed in on both sides at the same time and the tray in front of him suddenly moved slightly away from him. The sudden movement startled him and he quickly pulled his hands away and picked up his spoon again to keep eating. He glanced over at the women, they hadn’t noticed. Breathing a sigh of relief, he finished the only dinner he knew he was going to get. If he had to, he could get out of the chair by himself – as long as his arms were free!
Chad finished his dinner and his bottle, but the women were still laughing over the pictures – or whatever else they were looking at on Mel’s computer. He really had no idea. But now he was finished eating and he was still stuck in the chair. In a way, it was a bit like being stuck in the corner. But at least he was sitting down and he could move a little bit. He also had more to look at than two blank walls that were all too close to his eyes. But sitting stuck in the chair was still boring. He felt the need to pee again and let it out – reveling in how good it felt.
He was still sitting there, mostly forgotten, when Mel suddenly ushered Cassie and Sandy out. Mel came back to the kitchen and sat in one of the kitchen chairs near him. “You’re a mess,” she declared teasingly. “Just like a baby.”
He blushed. “Can I get up now?” he asked.
“When I’m ready,” she replied. She leaned her arm on the table and her head in her hand. “Dinner was good tonight,” she replied, “again. But I shouldn’t have to tell you that.”
He actually felt a wave of relief. “Thank you, Mistress. It means a lot to me to hear you say that. I was hoping to see how good it was myself though.”
“Maybe next time, Sissy.” She sat and stared at him. He wondered why.
“Cassie did a nice job on your hair last night.”
He wasn’t sure how to answer. He really wasn’t all that happy with what she had done to him – actually with several things she had done to him. “Did she?” he finally said.
Mel nodded. “It looked a lot better in the pictures through.”
He felt himself starting to blush a little bit. “I thought it looked way too feminine,” he admitted softly.
Mel smiled. “Perfect for you then. She said she used a curling iron on it last night. We’ll get you one tomorrow then Cassie can teach you how to use it.”
Chad looked at her horrified. He didn’t know how to answer. His entire life now was one humiliation piled on top of another!
“I heard you added some more makeup after you got to work today,” Mel continued when he didn’t say anything.
He blushed briefly again, then got worried. “I’m sorry, Mistress. I didn’t know you wouldn’t want me to.”
“I did want you to. I was very pleased to hear it.”
“Oh… Thank you,” he replied. Why would she say that?
“What made you decide to add the lipstick?”
He shrugged as best he could in his confining seat. “Robin suggested it. She said I looked too pale without it.”
The mention of Robin instantly sent a tiny bolt of annoyance through Mel’s body. The Robin woman again! She was starting to dislike her even more. There was no real reason for it, she just did. Was she pretty? Did Chad have a thing for her? She didn’t know. But obviously, this Robin had a lot of influence over him. Influence she was jealous of. Annoyed over Robin, Mel got up and released him from the confining highchair. “Finish cleaning up the kitchen now,” she ordered.
While Chad got busy cleaning up after dinner again, Mel walked into her bedroom to start preparing for later. She saw his uniform dress hanging on her closet door. She shook her head. As much as she would like seeing him in it tonight, it wasn’t going to happen. Not tonight at least. Tonight was about other things.
She went back out to the kitchen. “Stop what you’re doing for a few minutes.”
Chad turned the water off at the sink and looked at her questioningly.
“Go take your uniform home again and leave it there. Bring back one of your onesies instead.
Chad blinked. Take his uniform home? Why now? But he dutifully dropped into a quick curtsey and said “Yes, Mistress.” He quickly got his uniform and took it home and hung it in his closet. Then he found one of the onesies that she liked to lock him into. She hadn’t put him into one of them in quite a while. Why now? A few minutes later, he was back at her apartment again.
Mel took the onesie from Chad and held it up. She smiled at the sight of the babyish looking garment. “Get undressed. Just diapers and plastic panties.” Chad quickly complied and all too soon, Mel was helping fasten him into the babyish onesie. Fortunately, she didn’t add the lock. “Put your clothes in my clothes hamper,” she instructed him.
Chad did as he was told, but doing so reminded him of something. “Mistress, can I please do my laundry tonight? I’m running out of clothes.”
“Maybe later,” Mel replied. We have other things to do tonight. But right now, I want you to finish in the kitchen.
Chad went back to the kitchen. What did she have planned for tonight? He really had no idea. When the kitchen was done, Mel made him sit on the floor and drink another baby bottle of her tea. Chad wasn’t too happy about that. He suddenly had visions of her timing him again to see how soon he could pee.
But after he finished the bottle, Mel had him get started on the laundry and never once mentioned the timer. “Do all of my things first,” Mel instructed him as he began sorting through the clothes. “Don’t even think about doing any of your laundry till all of mine is done.”
Chad watched as Mel went back to her living room and picked up her laptop computer to keep working. He was relieved in several ways - no timing him to see how quickly he could pee, and more importantly, he really did need to get some laundry done.
Mel glanced at him occasionally as he worked around her apartment. Without being told, he cleaned her bathroom and dusted some furniture while the washer and dryer were running. Once in a while she got up to check his progress on the laundry. As she had instructed him, all of his things were still waiting to be cleaned. She watched the clock as he worked too. It was starting to get a bit later.
Just before he was about to start on his own laundry, she stopped him. “Put the laundry basket back into the bathroom now. It’s getting late and we have other things to do.”
Again Chad wondered what she had in mind, but his own laundry wasn’t even started yet. “But Mistress, can I at least get one load of my things into the washer first?”
“No, Sissy. It’s time for other things now.”
Again Chad had to wonder what she had in mind. Without realizing it, he was mentally bracing himself for more humiliation.
As Chad was carrying his dirty clothes back into her bathroom, she called after him. “Start the bathwater while you’re in there.”
As Chad turned the water on in the tub, he realized that she was going to be tying him up again and using him for her own little pleasures again. Ugh! He hated it, but he also loved it. What he hated was that she used him so hard and he was incapable of getting any relief. But why would she want him to run the bath water first? That was odd. Her bath usually came after she had abused him.
Mel walked into the bathroom with him. She watched as he poured some of the bath beads into the water. He glanced at her, questioning if he had put enough in. “A little bit more,” she told him with a smile.
As the tub was still filling, she unfastened his onesie and helped him out of it. Then she removed his plastic panties.
Chas was surprised when she removed his plastic panties. Was the bath for him instead?
“Lay down on the floor so I can remove your diapers,” she said. Chad felt a thrill of elation. It seemed that she wasn’t going to abuse him tonight. And a bath would really feel nice. As Mel was about to remove his diapers though, he suddenly realized that he had to pee slightly. He quickly stopped Mel from removing his diaper. “You might want to wait a moment on that,” he said, “I’m wetting myself right now.”
Mel smiled broadly at him. “Go right ahead,” she said sounding very satisfied.
After Mel had finally removed his diapers, Chad’s elation rose a whole lot more as Mel had him step into the warm scented bathwater. He laid back and allowed himself to relax and breathe in deeply. It felt so good!
Mel handed him her body sponge and he began cleaning himself off. The bath felt like a distinct pleasure. The only part he wasn’t crazy about was when Mel produced her razor and began removing the stray hairs from his body, making him totally smooth once again. “This is a lot easier now, since you’re shaving your own legs,” she commented. “From now on, make that part of your morning routine. I’m not going to mention it again.”
Chad felt a moment of bother about it, but it was no use resisting. “Yes, Mistress,” he replied.
“Lay back now and soak for a bit while I get the bedroom ready.”
Chad now knew exactly what to expect. She was going to tie him to her bed and probably torture him. He wasn’t looking forward to it. He concentrated instead on enjoying the pleasurable sensation of the warm bath while he still could - the one bright spot in his entire day.
Tuesday, March 16, 2010
The Bet - Chapter 19 (Wednesday – week 3 Part 3 of 5)
The Bet
by Karen Singer
Chapter 19 (Wednesday – week 3 Part 3 of 5)
“You threw him out? Right then? I don’t believe it!” Gloria exclaimed.
Mel nodded. “I really did. I just couldn’t take him anymore. Why should I if I wasn’t getting any satisfaction from him at all?”
“Good for you girl! I’m actually proud of you. I think the jerk deserved it!”
Mel smiled, “He really did.”
Gloria took another sip from her coffee. “So things between you and Chad are back to normal now?”
Mel sighed. “I hope so. At least they seem to be so far.”
“Are you still coming tomorrow night for your session?”
Mel brightened a bit. “I can’t wait. I don’t think he can either.” Both women giggled a bit at that since Gloria had planted the hypnotic suggestion in Chad that he would really enjoy the sessions.
“Listen, Mel, you mentioned yesterday something about having trouble with him and his pacifier?”
“Yeah, he forgets about it way too often.”
Gloria giggled again. “I can just picture him with it! Listen, do you want me to plant a few suggestions, mild ones anyway, about it tomorrow night?”
Mel thought about that. “What do you mean?”
“Just little things to make him want it more, that’s all.”
Mel smiled at the idea. “Why not? Just not too much though. I really should be doing that training myself.”
Gloria smiled. “I’ll just plant something tiny then, that’s all, and if you keep pushing him with it then between the two of us I don’t think he’ll be leaving it behind much longer.”
“Sounds good to me,” Mel replied, but just then her cell phone rang. “Hello?”
“Hi Mel. It’s Cassie.”
“Hi Cassie. Oh, thanks for the pictures from last night. They were great!”
“You’re welcome. I’ve got a lot more I can show you later. I’ll make you some copies if you want.”
“I’d love that. Will you do that for me?”
“Sure, Mel. Gladly. Hey, I noticed that Sissy was finally wearing a blouse today. It’s about time. I’m surprised you didn’t have him wearing one earlier.”
“It was his idea today.”
“Oh. Well, he could have padded his bra a bit under it. He didn’t seem to want to talk about that when I mentioned it. He did say though that someone else at work had told him the same thing.”
“Really? But he wouldn’t say anymore?”
“No. He didn’t want to talk. I just wanted to mention that the blouse and the rest of his makeup were a big improvement, that’s all.”
“Thanks Cassie. Wait a minute. What do you mean the rest of his makeup?”
“Well, I mean adding some color to his face. You know, like the lipstick and blush he was wearing. He didn’t look so pasty like he usually does.”
“That’s strange. He wasn’t wearing any lipstick when he left this morning.”
“Well he sure was when he met with me.”
“Thanks Cassie. I really appreciate it.”
“Oh! Mel! Wait a minute.”
“What is it?”
“Listen, I played with his backside again. He’s really loving it. And this time, no matter what I did to him, he didn’t get hard at all. I just thought you’d like to know.”
“Yeah, Cassie. That’s just what I wanted to know. That’s incredible. Thanks.”
“Mel, I think you should spend a little time with him on his backend, if you know what I mean. Maybe try sticking something up inside of him and pushing it in and out to see how he reacts. If you don’t have anything you can use, ask me, I’ve got a few things you can borrow. I just wanted you to know, you should try it.”
Mel thought for a moment. Cassie was really pushing this, so there must be something to it. She was going to have to explore it further for sure. And she hated to admit it, but she did have one thing she could use on him. “Thanks, Cassie. I was planning on spending some time on him tonight. I’ll explore it further then.”
“Good. Let me know, Mel.”
Chad was concentrating on his work really well after he got back to his desk, but a little while later that concentration was interrupted by the first signs that he was going to have to mess himself again. He thought back to his diaper change with Cassie. Had she put another suppository up inside of him? He didn’t really remember her doing it. He thought about it some more. That last time she had pulled her finger out and then stuck it back up inside of him again. That must have been it!
There was no denying the suppository so he didn’t even try. He hated having to spend the rest of the afternoon sitting in such a mess. He made a mental note to ask Mel it there was some way at all that he could alter the routine so it wouldn’t be so bad.
It was late afternoon, not long till work would be over, when Chad’s cell phone rang. “Hello?” he said into the phone.
“Hi Sissy,” Mel’s voice came over the line.
“Hi,” he replied.
“Oh Sissy, can’t you address me properly?”
He lowered his voice to almost a whisper. “Someone might hear me!”
“I don’t care. That’s not my problem.”
“Well it could be a problem for me!”
“Not in any way that I can see. In fact it’s going to be a bigger problem for you if you don’t!”
He was totally exasperated. “Hello Mistress,” he said just barely above a whisper, praying that nobody else would hear.
Mel giggled a bit. “That’s much better. See, no problem at all.”
He only hoped she was right.
“What can I do for you,” he asked more politely.
“Tonight, when you get home, change your diapers, but don’t put your uniform on. Just have it ready and bring it with you to my apartment. Then start dinner for me. Something nice. Ok?”
Her instructions were easy. He breathed a sigh of relief. “No problem. I’ll be glad to,” he replied.
“Good. See you later then.”
Robin stared over the top of the cubicle wall. She had heard Chad’s cell phone ring and she had heard him answer, but then his voice had dropped to such a whisper that she couldn’t hear him clearly anymore. She wasn’t at all sure, but she thought she had heard him say “Hello Mistress.” She just wasn’t at all sure she had heard it right. Couldn’t be! She was sure she had heard it wrong. But there was a tiny seed planted in her mind.
Chad hurried straight home after work and undressed. He jumped into the shower because it was the best way to get cleaned up. Then he got dressed again in mostly the same thing he had been wearing all day. The fresh diapers really felt good to him. It was such a relief to get out of the messy ones he had been wearing all afternoon. He really hated Mel’s suppositories – no matter who she had sticking them up inside of him or how much pleasure he had gotten in the process.
The only difference when he got dressed this time though, was that he took the time to pad his girdle out so that his blouse would look better. When he checked his reflection in the mirror afterwards, he realized that Robin had been right. The blouse did look better, and he supposed, overall, so did he. He reshined his low-heeled shoes and slipped into a pair with higher heels, grabbed his maid’s dress, and went over to Mel’s apartment. Fortunately, she wasn’t back from work yet.
He got started right away getting her dinner ready. There was this recipe he had been curious about that called for a lot of spices. Tonight would be the perfect time to try it.
Mel breezed in a little while later to the smell of pungent spices filling her apartment. “Mmm, smells good,” she said as she saw Sissy coming out of the kitchen to greet her.
“Hi, Mistress,” Sissy said dropping a quick curtsey.
“Hello, Sissy,” Mel replied with a smile in return.
Chad pointed back towards the kitchen. “I’ve really got to watch this stuff,” he said quickly.
“Go!” Mel ordered good-naturedly, then followed him towards the kitchen.
There was a cloud of steam rising from a large skillet on her stove and Sissy was busy stirring the contents with a wooden spoon. She took the time to look him over closely from across the room. “You look good today, Sissy. Real good.”
Chad tried to drop a quick curtsey and said a quick “Thank you,” before he went back to stirring their dinner intently. There was a knock on the door. Chad’s face went to a look of total worry as he held the wooden spoon up in the air.
Mel realized his plight, or more likely both of his plights. He was not only worried about answering the door, he had to keep working at their dinner and couldn’t stop just yet. “Don’t worry, I’ll get it,” she offered. Mel opened her front door and found both Cassie and Sandy there, carrying the highchair between them. “Hi girls,” Mel said.
“Hi, Mel,” Cassie replied. “We brought this over for you. We thought you might like to use it tonight.”
“Mel smiled broadly. “Would I ever!”
Cassie and Sandy were both laughing as they brought it inside. “Where do you want it?” Sandy asked.
“In the kitchen, beside the table,” Mel replied.
Sandy and Cassie continued on into the kitchen with the highchair. “Hi Sissy,” Cassie called out as she entered. “Smells good in here.”
“It does,” Sandy agreed. “Real good.”
Chad was about to say thank you to the two women till he saw what they had just brought in with them. All he could do then was to stare with disbelief at the object they were arranging near the table. Sandy saw him staring. “What? You didn’t think it was staying at our place, did you?”
Chad shook his head and went back to stirring the skillet. He would have much rather the all too humiliating chair stay as far away from him as possible. He stuck the spoon into the skillet and carefully tasted it. He closed his eyes. For non-fattening diet cooking, some dishes could be really good. He turned the stove off and grabbed two plates from the cupboard.
Mel watched him the whole time. Then she turned to her guests. “Would you like to stay for dinner?” she asked.
Cassie replied first. “I don’t know about Sandy, but it smells really interesting. I’d love to.”
“Definitely count me in too,” Sandy agreed.
“Three plates please, Sissy.” Mel ordered.
Chad looked at her with a very worried expression on his face. “Mistress, I don’t know if there’s enough for everybody. I wasn’t planning on company.”
Mel walked over and looked at the contents of the skillet. “Just divide it all out onto three plates. I’m sure we’ll be able to make do.”
Chad wanted to protest and ask what about his dinner, but Mel was staring at him as if to dare him to mention anything.
“Yes, Mistress,” he replied as he dropped a quick curtsey. A short while later, he was standing, stuffed into his corner, while all three women were laughing and enjoying themselves over the dinner he had prepared. He tried to listen to what they were saying, but mostly, it was useless. He was too far away. He hated standing in the corner like this, it was so demeaning. But he was becoming all to used to it now.
“Sissy, keep your feet still!” Mel’s voice lashed out at him.
Mel laughed with her guests. The dinner was really good. There could have been a bit more of it for each of them, but nobody mentioned it. And when Mel’s voice lashed out at Sissy to keep his feet still, they all laughed again.
“That reminds me,” Mel said. “I sort of got this strange idea for Sissy last night, but it needs a bit of help. I thought that you guys might be able to help me with it.”
“Well, for heaven’s sake, don’t keep us in suspense!” Sandy declared.
Mel dropped her voice to make sure that Chad couldn’t hear. “Last night, we were in the bar waiting for our table to get ready. I was sitting on a bar stool with my heel resting over one of the rungs, but when I got up, my heel was a bit higher than I’m used to wearing and it got caught over the rung. But it got me to thinking. When I had my heels resting on that rung, they were really hard to move. So I was thinking that maybe if I had something like that built for him to stand on, you know, where his heels would be resting on some kind of bar while he was standing there, then maybe it would be a lot more difficult for him to move his feet. What do you think?”
Cassie laughed. But Sandy had a thoughtful look on her face. “I wonder if that would really work,” she mused. “It certainly has possibilities. Of course we’d have to know how high to make the bar… and how wide… and how far from the wall… and”
“Stop!” Cassie cried. She looked back and forth between Mel and Sandy. “Are you really serious about this?”
“Sure,” Mel replied. “Why not?”
“Because once Sandy gets started on it, she won’t quit till it’s done!”
Sandy and Cassie both laughed, while Mel only slightly chuckled. Obviously there was some kind of inside joke about it between the two women.
“Ok,” Sandy said thoughtfully, “If he’s going to be standing on it in heels, then I guess his toes will have to be on the floor, but his heels will have to be raised off the floor. So how high do we make it?”
Chad stood silently in his corner, doing his best to move as little as possible, which was none too easy. The women were taking an eternity to finish eating, or more likely they were just talking now. He wondered what they were talking about. The highlight of his time in the corner was when he realized that he had to pee, and concentrating on the feeling as he let it out was pure heaven. Almost like sex. Unfortunately, it was over with all too soon.
He was startled when he suddenly realized that all three women were now standing behind him. He was careful to stand extra still. He heard them talking about his shoes and how closely he was scrunched into the wall. At one point, one of them, he thought it was Sandy, had bent down to examine his feet much closer. He was being really careful not to move his feet because that was the number one thing that Mel always yelled at him about.
It was with a huge relief when he heard Mel say, “Ok, Sissy. You can go clean up the kitchen now.”
He gratefully pulled himself out of the corner and shook himself a bit to get his blood flowing again. The three women were all standing behind him watching him… especially Mel. “Thank you, Mistress,” he said dropping a quick curtsey. He made a quick bee-line for the kitchen while Sandy and Cassie started laughing.
Hey Mel,” Cassie said. I’ve got some pictures for you if you want. We can download them straight to your computer.”
“Great!” Mel replied enthusiastically. “I can’t wait to see them.”
“I’ve got them at home,” Cassie replied. “I’ll get them real quick.”
Before Cassie could get out the door, Sandy yelled, “Wait!” She turned to Mel and whispered something. Mel smiled and nodded her head. “I’m coming with you!” Sandy declared.
by Karen Singer
Chapter 19 (Wednesday – week 3 Part 3 of 5)
“You threw him out? Right then? I don’t believe it!” Gloria exclaimed.
Mel nodded. “I really did. I just couldn’t take him anymore. Why should I if I wasn’t getting any satisfaction from him at all?”
“Good for you girl! I’m actually proud of you. I think the jerk deserved it!”
Mel smiled, “He really did.”
Gloria took another sip from her coffee. “So things between you and Chad are back to normal now?”
Mel sighed. “I hope so. At least they seem to be so far.”
“Are you still coming tomorrow night for your session?”
Mel brightened a bit. “I can’t wait. I don’t think he can either.” Both women giggled a bit at that since Gloria had planted the hypnotic suggestion in Chad that he would really enjoy the sessions.
“Listen, Mel, you mentioned yesterday something about having trouble with him and his pacifier?”
“Yeah, he forgets about it way too often.”
Gloria giggled again. “I can just picture him with it! Listen, do you want me to plant a few suggestions, mild ones anyway, about it tomorrow night?”
Mel thought about that. “What do you mean?”
“Just little things to make him want it more, that’s all.”
Mel smiled at the idea. “Why not? Just not too much though. I really should be doing that training myself.”
Gloria smiled. “I’ll just plant something tiny then, that’s all, and if you keep pushing him with it then between the two of us I don’t think he’ll be leaving it behind much longer.”
“Sounds good to me,” Mel replied, but just then her cell phone rang. “Hello?”
“Hi Mel. It’s Cassie.”
“Hi Cassie. Oh, thanks for the pictures from last night. They were great!”
“You’re welcome. I’ve got a lot more I can show you later. I’ll make you some copies if you want.”
“I’d love that. Will you do that for me?”
“Sure, Mel. Gladly. Hey, I noticed that Sissy was finally wearing a blouse today. It’s about time. I’m surprised you didn’t have him wearing one earlier.”
“It was his idea today.”
“Oh. Well, he could have padded his bra a bit under it. He didn’t seem to want to talk about that when I mentioned it. He did say though that someone else at work had told him the same thing.”
“Really? But he wouldn’t say anymore?”
“No. He didn’t want to talk. I just wanted to mention that the blouse and the rest of his makeup were a big improvement, that’s all.”
“Thanks Cassie. Wait a minute. What do you mean the rest of his makeup?”
“Well, I mean adding some color to his face. You know, like the lipstick and blush he was wearing. He didn’t look so pasty like he usually does.”
“That’s strange. He wasn’t wearing any lipstick when he left this morning.”
“Well he sure was when he met with me.”
“Thanks Cassie. I really appreciate it.”
“Oh! Mel! Wait a minute.”
“What is it?”
“Listen, I played with his backside again. He’s really loving it. And this time, no matter what I did to him, he didn’t get hard at all. I just thought you’d like to know.”
“Yeah, Cassie. That’s just what I wanted to know. That’s incredible. Thanks.”
“Mel, I think you should spend a little time with him on his backend, if you know what I mean. Maybe try sticking something up inside of him and pushing it in and out to see how he reacts. If you don’t have anything you can use, ask me, I’ve got a few things you can borrow. I just wanted you to know, you should try it.”
Mel thought for a moment. Cassie was really pushing this, so there must be something to it. She was going to have to explore it further for sure. And she hated to admit it, but she did have one thing she could use on him. “Thanks, Cassie. I was planning on spending some time on him tonight. I’ll explore it further then.”
“Good. Let me know, Mel.”
Chad was concentrating on his work really well after he got back to his desk, but a little while later that concentration was interrupted by the first signs that he was going to have to mess himself again. He thought back to his diaper change with Cassie. Had she put another suppository up inside of him? He didn’t really remember her doing it. He thought about it some more. That last time she had pulled her finger out and then stuck it back up inside of him again. That must have been it!
There was no denying the suppository so he didn’t even try. He hated having to spend the rest of the afternoon sitting in such a mess. He made a mental note to ask Mel it there was some way at all that he could alter the routine so it wouldn’t be so bad.
It was late afternoon, not long till work would be over, when Chad’s cell phone rang. “Hello?” he said into the phone.
“Hi Sissy,” Mel’s voice came over the line.
“Hi,” he replied.
“Oh Sissy, can’t you address me properly?”
He lowered his voice to almost a whisper. “Someone might hear me!”
“I don’t care. That’s not my problem.”
“Well it could be a problem for me!”
“Not in any way that I can see. In fact it’s going to be a bigger problem for you if you don’t!”
He was totally exasperated. “Hello Mistress,” he said just barely above a whisper, praying that nobody else would hear.
Mel giggled a bit. “That’s much better. See, no problem at all.”
He only hoped she was right.
“What can I do for you,” he asked more politely.
“Tonight, when you get home, change your diapers, but don’t put your uniform on. Just have it ready and bring it with you to my apartment. Then start dinner for me. Something nice. Ok?”
Her instructions were easy. He breathed a sigh of relief. “No problem. I’ll be glad to,” he replied.
“Good. See you later then.”
Robin stared over the top of the cubicle wall. She had heard Chad’s cell phone ring and she had heard him answer, but then his voice had dropped to such a whisper that she couldn’t hear him clearly anymore. She wasn’t at all sure, but she thought she had heard him say “Hello Mistress.” She just wasn’t at all sure she had heard it right. Couldn’t be! She was sure she had heard it wrong. But there was a tiny seed planted in her mind.
Chad hurried straight home after work and undressed. He jumped into the shower because it was the best way to get cleaned up. Then he got dressed again in mostly the same thing he had been wearing all day. The fresh diapers really felt good to him. It was such a relief to get out of the messy ones he had been wearing all afternoon. He really hated Mel’s suppositories – no matter who she had sticking them up inside of him or how much pleasure he had gotten in the process.
The only difference when he got dressed this time though, was that he took the time to pad his girdle out so that his blouse would look better. When he checked his reflection in the mirror afterwards, he realized that Robin had been right. The blouse did look better, and he supposed, overall, so did he. He reshined his low-heeled shoes and slipped into a pair with higher heels, grabbed his maid’s dress, and went over to Mel’s apartment. Fortunately, she wasn’t back from work yet.
He got started right away getting her dinner ready. There was this recipe he had been curious about that called for a lot of spices. Tonight would be the perfect time to try it.
Mel breezed in a little while later to the smell of pungent spices filling her apartment. “Mmm, smells good,” she said as she saw Sissy coming out of the kitchen to greet her.
“Hi, Mistress,” Sissy said dropping a quick curtsey.
“Hello, Sissy,” Mel replied with a smile in return.
Chad pointed back towards the kitchen. “I’ve really got to watch this stuff,” he said quickly.
“Go!” Mel ordered good-naturedly, then followed him towards the kitchen.
There was a cloud of steam rising from a large skillet on her stove and Sissy was busy stirring the contents with a wooden spoon. She took the time to look him over closely from across the room. “You look good today, Sissy. Real good.”
Chad tried to drop a quick curtsey and said a quick “Thank you,” before he went back to stirring their dinner intently. There was a knock on the door. Chad’s face went to a look of total worry as he held the wooden spoon up in the air.
Mel realized his plight, or more likely both of his plights. He was not only worried about answering the door, he had to keep working at their dinner and couldn’t stop just yet. “Don’t worry, I’ll get it,” she offered. Mel opened her front door and found both Cassie and Sandy there, carrying the highchair between them. “Hi girls,” Mel said.
“Hi, Mel,” Cassie replied. “We brought this over for you. We thought you might like to use it tonight.”
“Mel smiled broadly. “Would I ever!”
Cassie and Sandy were both laughing as they brought it inside. “Where do you want it?” Sandy asked.
“In the kitchen, beside the table,” Mel replied.
Sandy and Cassie continued on into the kitchen with the highchair. “Hi Sissy,” Cassie called out as she entered. “Smells good in here.”
“It does,” Sandy agreed. “Real good.”
Chad was about to say thank you to the two women till he saw what they had just brought in with them. All he could do then was to stare with disbelief at the object they were arranging near the table. Sandy saw him staring. “What? You didn’t think it was staying at our place, did you?”
Chad shook his head and went back to stirring the skillet. He would have much rather the all too humiliating chair stay as far away from him as possible. He stuck the spoon into the skillet and carefully tasted it. He closed his eyes. For non-fattening diet cooking, some dishes could be really good. He turned the stove off and grabbed two plates from the cupboard.
Mel watched him the whole time. Then she turned to her guests. “Would you like to stay for dinner?” she asked.
Cassie replied first. “I don’t know about Sandy, but it smells really interesting. I’d love to.”
“Definitely count me in too,” Sandy agreed.
“Three plates please, Sissy.” Mel ordered.
Chad looked at her with a very worried expression on his face. “Mistress, I don’t know if there’s enough for everybody. I wasn’t planning on company.”
Mel walked over and looked at the contents of the skillet. “Just divide it all out onto three plates. I’m sure we’ll be able to make do.”
Chad wanted to protest and ask what about his dinner, but Mel was staring at him as if to dare him to mention anything.
“Yes, Mistress,” he replied as he dropped a quick curtsey. A short while later, he was standing, stuffed into his corner, while all three women were laughing and enjoying themselves over the dinner he had prepared. He tried to listen to what they were saying, but mostly, it was useless. He was too far away. He hated standing in the corner like this, it was so demeaning. But he was becoming all to used to it now.
“Sissy, keep your feet still!” Mel’s voice lashed out at him.
Mel laughed with her guests. The dinner was really good. There could have been a bit more of it for each of them, but nobody mentioned it. And when Mel’s voice lashed out at Sissy to keep his feet still, they all laughed again.
“That reminds me,” Mel said. “I sort of got this strange idea for Sissy last night, but it needs a bit of help. I thought that you guys might be able to help me with it.”
“Well, for heaven’s sake, don’t keep us in suspense!” Sandy declared.
Mel dropped her voice to make sure that Chad couldn’t hear. “Last night, we were in the bar waiting for our table to get ready. I was sitting on a bar stool with my heel resting over one of the rungs, but when I got up, my heel was a bit higher than I’m used to wearing and it got caught over the rung. But it got me to thinking. When I had my heels resting on that rung, they were really hard to move. So I was thinking that maybe if I had something like that built for him to stand on, you know, where his heels would be resting on some kind of bar while he was standing there, then maybe it would be a lot more difficult for him to move his feet. What do you think?”
Cassie laughed. But Sandy had a thoughtful look on her face. “I wonder if that would really work,” she mused. “It certainly has possibilities. Of course we’d have to know how high to make the bar… and how wide… and how far from the wall… and”
“Stop!” Cassie cried. She looked back and forth between Mel and Sandy. “Are you really serious about this?”
“Sure,” Mel replied. “Why not?”
“Because once Sandy gets started on it, she won’t quit till it’s done!”
Sandy and Cassie both laughed, while Mel only slightly chuckled. Obviously there was some kind of inside joke about it between the two women.
“Ok,” Sandy said thoughtfully, “If he’s going to be standing on it in heels, then I guess his toes will have to be on the floor, but his heels will have to be raised off the floor. So how high do we make it?”
Chad stood silently in his corner, doing his best to move as little as possible, which was none too easy. The women were taking an eternity to finish eating, or more likely they were just talking now. He wondered what they were talking about. The highlight of his time in the corner was when he realized that he had to pee, and concentrating on the feeling as he let it out was pure heaven. Almost like sex. Unfortunately, it was over with all too soon.
He was startled when he suddenly realized that all three women were now standing behind him. He was careful to stand extra still. He heard them talking about his shoes and how closely he was scrunched into the wall. At one point, one of them, he thought it was Sandy, had bent down to examine his feet much closer. He was being really careful not to move his feet because that was the number one thing that Mel always yelled at him about.
It was with a huge relief when he heard Mel say, “Ok, Sissy. You can go clean up the kitchen now.”
He gratefully pulled himself out of the corner and shook himself a bit to get his blood flowing again. The three women were all standing behind him watching him… especially Mel. “Thank you, Mistress,” he said dropping a quick curtsey. He made a quick bee-line for the kitchen while Sandy and Cassie started laughing.
Hey Mel,” Cassie said. I’ve got some pictures for you if you want. We can download them straight to your computer.”
“Great!” Mel replied enthusiastically. “I can’t wait to see them.”
“I’ve got them at home,” Cassie replied. “I’ll get them real quick.”
Before Cassie could get out the door, Sandy yelled, “Wait!” She turned to Mel and whispered something. Mel smiled and nodded her head. “I’m coming with you!” Sandy declared.
Friday, March 12, 2010
The Bet - Chapter 19 (Wednesday – week 3 Part 2 of 5)
The Bet
by Karen Singer
Chapter 19 (Wednesday – week 3 Part 2 of 5)
Chad sat down at his desk and noticed that Robin must have turned his computer off last night. He mentally thanked her, the company didn’t like for the computers to be left up and running every night. As soon as he could, he opened up his spreadsheet for tracking his progress on the bet. Forty-four days to go. And eternity! He had done really well holding back yesterday, but he didn’t really know how long he had held it. He put down thirty minutes as a conservative estimate and closed the spreadsheet. Still on track!
“Morning Chad,” Robin called as she walked past his cubicle on the way to hers.
“Morning,” he called back as he started opening the project they were working on. He needed to do a lot more with the animations they had planned on today.
“Hey Chad,” Robin said a few minutes later, from the entrance to his cubicle. He was startled because he hadn’t heard her come back. “What happened to you yesterday?”
He turned around to face her. But before he could say anything, she let out a little squeal. “Chad! Look at you. You’ve had your hair done… and finally… you’re wearing a blouse!”
He could feel himself blushing. “Yeah, well…”
She came all the way into his cubicle so she could see him closer. “Where did you get your hair done?” she asked.
“A friend,” he replied.
“Mel? Your makeup lady?”
“No, someone else.”
“Well, whoever it was did a nice job. I like it.”
“I think it looks too girly,” he replied.
“Well for heaven’s sake! Look at the way your dressed. And you’re worried about it being too girly? Is that how you asked her to cut it?”
“No, she just did it.”
“Well, I like it. And finally… finally… you’re wearing a blouse! Very pretty, by the way. It’s a big improvement.”
“Improvement?”
“Yeah. Seeing how everything else you’re wearing is female. It looked dorky before… stupid!”
“Maybe,” he admitted.
“You know,” she said, “that blouse would look a lot better with some padding in your bra. A lot better! You should do it.”
He rolled his eyes. Now he was sorry he had decided to wear the blouse. “That’s ok,” he replied. I like it just the way it is.”
“But it needs something!” she replied. “It’s tapered for breasts. It doesn’t look right without anything! You need breasts!”
She was pushing at him. Asking him to do something he didn’t want to do. “That’s alright. I like it the way it is!” he replied a bit too forcefully before she could argue anymore.
She backed off and just stared at him for a second. Had he yelled at her? She wasn’t sure. But he certainly hadn’t been very polite! “Suit yourself. I’m only trying to help,” she replied, sounding just as put off by him as she felt. She turned to walk away and stopped. “You know, you could really use some color on your face too. Just eye makeup and foundation makes you look too pale. A little lipstick wouldn’t hurt you.” She left then, not wanting to stay around him any more. In fact, her last comment, while totally practical and the way she really felt, had been said more as a way to strike back at him for his attitude a few moments earlier. She tried to force him out of her head as she got down to work.
Chad stared at his computer screen trying to concentrate on his work, but all he could think about was his last conversation with Robin. He hadn’t meant to be so forceful, it had just happened. But damn, the woman could push. Why couldn’t she leave things alone? She was always after him, peppering him with questions about what was going on, and he didn’t want to tell her. He wasn’t going to tell her! It was none of her business! And now she wanted him to pad his bra? Well, the cups of his girdle anyway. It wasn’t going to happen!
But he still felt bad about the way he had spoken to her and she had been obviously put off. And she had shut his computer down for him last night so he wouldn’t get in trouble. Damn her! Damn all women! Why couldn’t life be simple? And so what if his face looked pale? Mel hadn’t said he had to wear anymore makeup. He didn’t have to please Robin – only Mel!
He sat back and sighed. But Robin was still a friend. One of the only friends he had left – maybe THE only friend. He shouldn’t have gotten so angry with her. But damn, the woman had been pushing at him again. Damn her! He pulled his purse out of his desk drawer and found the little compact with the mirror in it. He looked at his face as best as he could. He needed a peace offering. Some small way to say he was sorry - friend or not, he did have to work with the woman. He selected a lipstick… and then some blush… and then something to fix the tiny smeared spot from breakfast.
“Robin,” he said contritely from the entrance to her cubicle.
“What?” she asked without turning around. She was still put off.
“Is this any better?”
His question startled her, as did the tone of his voice. She turned around and was shocked. She smiled. “Yeah, a lot better.”
“Look, I’m sorry for my attitude a few minutes ago. This isn’t easy for me. And when you push so hard sometimes, I guess I get frustrated. That’s all.”
She looked a bit sheepish. “I know I can be pushy sometimes, but that’s just the way I am.” She suddenly had a questioning look on her face. “If it’s so hard for you, then why do you do it?”
“I can’t tell you that.”
“Why not? Why can’t you just come out and admit that you’re doing it because you like it?” She was sounding angrier again.
He shook his head. “You don’t understand.”
“Then explain it to me!”
“I can’t!”
“Why not?”
“Because… it’s complicated!”
She threw her hands up in the air in exasperation. “Get out of here!”
In the middle of the morning, Mel checked her computer between clients and found an email from Cassie. She was very surprised to see an email since Cassie always called. When she opened it, the email just said that she thought Mel would like to see some pictures of Sissy from last night. There were three pictures enclosed. The first picture was a close-up of his face. It showed him right after Cassie must have finished fixing his hair. She looked closer. His hair looked different in the picture than the way it looked this morning. Much more feminine and really pretty… and not just because of the pink bow tied into it. The difference she decided was that it was fixed the way a woman would fix it. Obviously Cassie had used a curling iron on it.
She opened the second picture and almost laughed. Chad’s hair was totally covered in bows and hairclips of all kinds. She looked closer. She could hardly see any of his hair at all.
She opened the third picture and smiled. Chad playing with the baby toys on the floor. It was actually cute.
She went back to the first picture and stared at it. Cassie really had done a nice job on his hair. She made a mental note to talk about it with her later. Unfortunately, she had another client to meet just then. But she did do one thing quickly before she closed the email. She forwarded it to Chad at work.
Chad opened the email from Mel with a little trepidation. He was surprised to see the email because she had never emailed him before. He was happy to see however that the email didn’t contain any instructions for him, just some pictures. He glanced around to make sure that nobody was walking past his cubicle that could see in – especially Robin. Then he opened the first picture. He stared at himself for a long time. It was the first chance he had to see what Cassie had really done to his hair. It looked far more feminine in the picture than it did when he had seen it in his bathroom mirror this morning. Maybe it was the pink bow. But he really knew that the bow had very little to do with it.
He opened the second picture and let out a small laugh of surprise. His head was completely covered in their hairclips. It really was a funny picture.
He opened the third picture - him playing on the blanket with the baby toys. He was very relieved that more embarrassing pictures weren’t included. These were all “safe.” As far as he could tell from the email, that’s all that Cassie had sent to Mel. He opened up the first picture and stared at it again. Had he really looked like that last night – with the makeup and the big pink bow? Embarrassing! He closed the picture and quickly deleted the email to make sure that nobody at work would ever “accidentally” see the pictures.
“Do you want to come to break with me?” Robin’s voice asked from behind him.
He turned around, horrified to see her standing there. Had she seen any of the pictures? She didn’t act like she had. She was just standing there waiting for an answer. He shook his head. “No thanks,” he replied, praying that she hadn’t really seen anything.
“Ok,” she replied as she walked off.
He breathed a sigh of relief. It looked like it was ok.
Late in the morning, Mel checked her messages and called one of the numbers back. “Hi Gloria, it’s Mel.”
“Hi Mel. I was just wondering how you and Chad are getting along now.”
“Much better. And Gloria, I’ve really got to thank you for getting my head straight yesterday. I guess it was kind of a wakeup call.”
“So things are all honky-dory between you two again?”
“As far as I can tell anyway.”
“Good. So how about your date last night?”
“Ugh! I can’t begin to tell you how awful it was – from start to finish!”
Gloria laughed. “Want to tell me about it during lunch?”
This time Mel laughed. “Sure. And this time, I’m buying.”
Robin watched as Chad hurried out to his car at lunchtime. She knew exactly where he was going, just not exactly what he was doing. It frustrated her a bit, but then there was a lot about him lately that frustrated her. Not wanting to think about it anymore, she purposely drove off in the opposite direction.
While the change in her routine felt refreshing and good, it only served to remind her more that she had been following Chad everyday. As she ordered lunch in a place she hadn’t been to in weeks now, her mind dwelled on him. What was he really doing at that gym? While she ate, she continued to think about it. She couldn’t help it. She knew that she needed to start going to lunch with some of her girlfriends instead! It would be so much better than thinking about Chad while she ate. But then, even during their breaks at work, Chad was a major part of every conversation. There was no getting away from it.
By the time she finished eating, she realized that she was more determined than ever to get to the bottom of what was really going on. Sissy? Was he really calling himself that at the gym? It didn’t seem likely, but by the way the receptionist had reacted, she actually believed it. How about anywhere else? Where else did he go? What else did he do with his life? How could she find out? He was like one big puzzle – and she loved puzzles!
Chad walked into the gym and saw the receptionist immediately put a big smile on her face. Was there a twinkle of mischief in her eyes as well? “Hello Sissy,” she greeted him all too loudly.
He hated his life. He dropped a quick curtsey to her and said a simple “Hello.” The receptionist instantly began giggling. Why? She had seen him do it before. Fortunately, she immediately went in search of Cassie. She and Cassie were back a few moments later.
“Hi, Sissy,” Cassie called as soon as she spotted him. Chad curtseyed to her and returned the greeting. Then he followed her back to their usual office. While he began getting undressed, Cassie pulled one of the baby bottles out of his bag for him. “I like your blouse today,” she said as he was getting undressed.
He wasn’t sure how to answer. “Thanks,” he replied.
“It could use a bit of padding in the breasts though.”
Ugh! Once again he was sorry he had worn it. “I know,” he replied.
She looked up at him as he was pulling his pants off. “Then why didn’t you pad them?”
He shook his head. “I was at work before I found out.”
“You found out at work?”
He blushed. “Yeah, from one of the women I work with.”
“What did she say?”
He shook his head. “I’d rather not talk about it.”
She shrugged her shoulders. “I was just asking. By the way, I’m glad you finally added some color to your face. It looks much better.”
He didn’t want to tell her that it was because of Robin that he had done it. “Thanks,” he replied simply. He suddenly felt the need to pee again. It would be better to do it now than after she had changed him.
She saw him stop undressing for a moment and just stand there. “What’s wrong?”
“I’m wetting myself again. Better now than later.” Cassie laughed.
A few minutest later, Chad was once again sucking on the baby bottle while Cassie was rubbing baby lotion all too intimately into the front of his private areas. She watched him closely. He was staring at her. Even with the bottle in his mouth she could tell there was a worried look on his face. His chastity device prevented her from really touching him where she needed to, but she did her best to excite him anyway. His bottle was half-finished when she finally smiled and pulled her hands away. He had never stopped staring at her. He had never stopped sucking on his bottle. And he had never even begun to get hard. “You’re definitely getting a lot better,” she said. He said nothing, but she thought she saw him blush a bit.
She remembered all too well how he had reacted last night when they had played with her little toy in his asshole. He had done amazingly well then too. Her voice was almost a whisper. “Would you like me to play with your backside a bit again?”
He didn’t know how to answer. Yes he did… but no he didn’t. When she did it, it was the closest thing to a sexual sensation he could feel – other than peeing. But at the same time, it disturbed him way too much. He couldn’t decide.
Her voice was still soft. “You really seemed to like it last night. I don’t have to do it today, I was just wondering.”
She was leaving him a way out. But he had liked it last night. A lot! Without realizing it, he let out a small whimper in his indecision. His need for sexual relief was so much. But the humiliation!
She smiled down at him and took the bottle away from him. “Roll over. I’ll just do it a tiny bit for you, ok?”
He needed it, but he hated it. He despised the fact that it should affect him like it did, but he also wanted it. She put her hand on his hip and pushed. He rolled over and brought his knees under him, lifting his rear end high into the air – totally exposed and open to her touch. Again, he whimpered in his need, and frustration, and humiliation.
Cassie lubed her hands again with the baby lotion and began massaging his backside again. Within moments, she could feel him moving almost rhythmically back and forth under her touch, and she hadn’t even gotten to the good part yet. But when she did start to go there, his movements stopped, completely. She touched him lightly there again and saw the quick shock that seemed to run up his spine. She pulled her finger away, then did it again. No shock this time, just acceptance and waiting. She pushed till her fingertip entered him, then she wiggled it. He arched his back and neck at the sensation. She pulled her finger away again and he almost collapsed back into his original position.
Chad closed his eyes and concentrated on her hands. Once again he felt her place her finger, this time ever so lightly against him. He waited patiently wanting more. Very, very slowly, he felt the pressure increasing, till her finger finally slipped in. Then her finger paused. Would she wiggle it again? But now the pressure was increasing. He could feel her finger going deeper inside of him, then deeper still. He unconsciously let out a small moan. Her finger pulled back, but not out, then pushed in again. Then she repeated the motion. Then she did it faster. All of his muscles began to contract. It felt amazing! He wanted more! But suddenly her finger was gone. No! A minute later it was back again pushing deep inside him. Yes! But then it was gone again. Why? He wanted more. But suddenly she was pushing on him.
“Roll over again,” she said softly and kindly.
He felt so frustrated as he rolled back over again onto his back. He accepted the baby bottle again and he put it back to his lips while he felt her diapering him again.
She leaned over him. Her voice was almost a whisper. “You did really well today, didn’t you!” It was at that point that he realized that his chastity device had never hurt him at all. Not one little bit. And during that last part, he hadn’t even thought about it.
by Karen Singer
Chapter 19 (Wednesday – week 3 Part 2 of 5)
Chad sat down at his desk and noticed that Robin must have turned his computer off last night. He mentally thanked her, the company didn’t like for the computers to be left up and running every night. As soon as he could, he opened up his spreadsheet for tracking his progress on the bet. Forty-four days to go. And eternity! He had done really well holding back yesterday, but he didn’t really know how long he had held it. He put down thirty minutes as a conservative estimate and closed the spreadsheet. Still on track!
“Morning Chad,” Robin called as she walked past his cubicle on the way to hers.
“Morning,” he called back as he started opening the project they were working on. He needed to do a lot more with the animations they had planned on today.
“Hey Chad,” Robin said a few minutes later, from the entrance to his cubicle. He was startled because he hadn’t heard her come back. “What happened to you yesterday?”
He turned around to face her. But before he could say anything, she let out a little squeal. “Chad! Look at you. You’ve had your hair done… and finally… you’re wearing a blouse!”
He could feel himself blushing. “Yeah, well…”
She came all the way into his cubicle so she could see him closer. “Where did you get your hair done?” she asked.
“A friend,” he replied.
“Mel? Your makeup lady?”
“No, someone else.”
“Well, whoever it was did a nice job. I like it.”
“I think it looks too girly,” he replied.
“Well for heaven’s sake! Look at the way your dressed. And you’re worried about it being too girly? Is that how you asked her to cut it?”
“No, she just did it.”
“Well, I like it. And finally… finally… you’re wearing a blouse! Very pretty, by the way. It’s a big improvement.”
“Improvement?”
“Yeah. Seeing how everything else you’re wearing is female. It looked dorky before… stupid!”
“Maybe,” he admitted.
“You know,” she said, “that blouse would look a lot better with some padding in your bra. A lot better! You should do it.”
He rolled his eyes. Now he was sorry he had decided to wear the blouse. “That’s ok,” he replied. I like it just the way it is.”
“But it needs something!” she replied. “It’s tapered for breasts. It doesn’t look right without anything! You need breasts!”
She was pushing at him. Asking him to do something he didn’t want to do. “That’s alright. I like it the way it is!” he replied a bit too forcefully before she could argue anymore.
She backed off and just stared at him for a second. Had he yelled at her? She wasn’t sure. But he certainly hadn’t been very polite! “Suit yourself. I’m only trying to help,” she replied, sounding just as put off by him as she felt. She turned to walk away and stopped. “You know, you could really use some color on your face too. Just eye makeup and foundation makes you look too pale. A little lipstick wouldn’t hurt you.” She left then, not wanting to stay around him any more. In fact, her last comment, while totally practical and the way she really felt, had been said more as a way to strike back at him for his attitude a few moments earlier. She tried to force him out of her head as she got down to work.
Chad stared at his computer screen trying to concentrate on his work, but all he could think about was his last conversation with Robin. He hadn’t meant to be so forceful, it had just happened. But damn, the woman could push. Why couldn’t she leave things alone? She was always after him, peppering him with questions about what was going on, and he didn’t want to tell her. He wasn’t going to tell her! It was none of her business! And now she wanted him to pad his bra? Well, the cups of his girdle anyway. It wasn’t going to happen!
But he still felt bad about the way he had spoken to her and she had been obviously put off. And she had shut his computer down for him last night so he wouldn’t get in trouble. Damn her! Damn all women! Why couldn’t life be simple? And so what if his face looked pale? Mel hadn’t said he had to wear anymore makeup. He didn’t have to please Robin – only Mel!
He sat back and sighed. But Robin was still a friend. One of the only friends he had left – maybe THE only friend. He shouldn’t have gotten so angry with her. But damn, the woman had been pushing at him again. Damn her! He pulled his purse out of his desk drawer and found the little compact with the mirror in it. He looked at his face as best as he could. He needed a peace offering. Some small way to say he was sorry - friend or not, he did have to work with the woman. He selected a lipstick… and then some blush… and then something to fix the tiny smeared spot from breakfast.
“Robin,” he said contritely from the entrance to her cubicle.
“What?” she asked without turning around. She was still put off.
“Is this any better?”
His question startled her, as did the tone of his voice. She turned around and was shocked. She smiled. “Yeah, a lot better.”
“Look, I’m sorry for my attitude a few minutes ago. This isn’t easy for me. And when you push so hard sometimes, I guess I get frustrated. That’s all.”
She looked a bit sheepish. “I know I can be pushy sometimes, but that’s just the way I am.” She suddenly had a questioning look on her face. “If it’s so hard for you, then why do you do it?”
“I can’t tell you that.”
“Why not? Why can’t you just come out and admit that you’re doing it because you like it?” She was sounding angrier again.
He shook his head. “You don’t understand.”
“Then explain it to me!”
“I can’t!”
“Why not?”
“Because… it’s complicated!”
She threw her hands up in the air in exasperation. “Get out of here!”
In the middle of the morning, Mel checked her computer between clients and found an email from Cassie. She was very surprised to see an email since Cassie always called. When she opened it, the email just said that she thought Mel would like to see some pictures of Sissy from last night. There were three pictures enclosed. The first picture was a close-up of his face. It showed him right after Cassie must have finished fixing his hair. She looked closer. His hair looked different in the picture than the way it looked this morning. Much more feminine and really pretty… and not just because of the pink bow tied into it. The difference she decided was that it was fixed the way a woman would fix it. Obviously Cassie had used a curling iron on it.
She opened the second picture and almost laughed. Chad’s hair was totally covered in bows and hairclips of all kinds. She looked closer. She could hardly see any of his hair at all.
She opened the third picture and smiled. Chad playing with the baby toys on the floor. It was actually cute.
She went back to the first picture and stared at it. Cassie really had done a nice job on his hair. She made a mental note to talk about it with her later. Unfortunately, she had another client to meet just then. But she did do one thing quickly before she closed the email. She forwarded it to Chad at work.
Chad opened the email from Mel with a little trepidation. He was surprised to see the email because she had never emailed him before. He was happy to see however that the email didn’t contain any instructions for him, just some pictures. He glanced around to make sure that nobody was walking past his cubicle that could see in – especially Robin. Then he opened the first picture. He stared at himself for a long time. It was the first chance he had to see what Cassie had really done to his hair. It looked far more feminine in the picture than it did when he had seen it in his bathroom mirror this morning. Maybe it was the pink bow. But he really knew that the bow had very little to do with it.
He opened the second picture and let out a small laugh of surprise. His head was completely covered in their hairclips. It really was a funny picture.
He opened the third picture - him playing on the blanket with the baby toys. He was very relieved that more embarrassing pictures weren’t included. These were all “safe.” As far as he could tell from the email, that’s all that Cassie had sent to Mel. He opened up the first picture and stared at it again. Had he really looked like that last night – with the makeup and the big pink bow? Embarrassing! He closed the picture and quickly deleted the email to make sure that nobody at work would ever “accidentally” see the pictures.
“Do you want to come to break with me?” Robin’s voice asked from behind him.
He turned around, horrified to see her standing there. Had she seen any of the pictures? She didn’t act like she had. She was just standing there waiting for an answer. He shook his head. “No thanks,” he replied, praying that she hadn’t really seen anything.
“Ok,” she replied as she walked off.
He breathed a sigh of relief. It looked like it was ok.
Late in the morning, Mel checked her messages and called one of the numbers back. “Hi Gloria, it’s Mel.”
“Hi Mel. I was just wondering how you and Chad are getting along now.”
“Much better. And Gloria, I’ve really got to thank you for getting my head straight yesterday. I guess it was kind of a wakeup call.”
“So things are all honky-dory between you two again?”
“As far as I can tell anyway.”
“Good. So how about your date last night?”
“Ugh! I can’t begin to tell you how awful it was – from start to finish!”
Gloria laughed. “Want to tell me about it during lunch?”
This time Mel laughed. “Sure. And this time, I’m buying.”
Robin watched as Chad hurried out to his car at lunchtime. She knew exactly where he was going, just not exactly what he was doing. It frustrated her a bit, but then there was a lot about him lately that frustrated her. Not wanting to think about it anymore, she purposely drove off in the opposite direction.
While the change in her routine felt refreshing and good, it only served to remind her more that she had been following Chad everyday. As she ordered lunch in a place she hadn’t been to in weeks now, her mind dwelled on him. What was he really doing at that gym? While she ate, she continued to think about it. She couldn’t help it. She knew that she needed to start going to lunch with some of her girlfriends instead! It would be so much better than thinking about Chad while she ate. But then, even during their breaks at work, Chad was a major part of every conversation. There was no getting away from it.
By the time she finished eating, she realized that she was more determined than ever to get to the bottom of what was really going on. Sissy? Was he really calling himself that at the gym? It didn’t seem likely, but by the way the receptionist had reacted, she actually believed it. How about anywhere else? Where else did he go? What else did he do with his life? How could she find out? He was like one big puzzle – and she loved puzzles!
Chad walked into the gym and saw the receptionist immediately put a big smile on her face. Was there a twinkle of mischief in her eyes as well? “Hello Sissy,” she greeted him all too loudly.
He hated his life. He dropped a quick curtsey to her and said a simple “Hello.” The receptionist instantly began giggling. Why? She had seen him do it before. Fortunately, she immediately went in search of Cassie. She and Cassie were back a few moments later.
“Hi, Sissy,” Cassie called as soon as she spotted him. Chad curtseyed to her and returned the greeting. Then he followed her back to their usual office. While he began getting undressed, Cassie pulled one of the baby bottles out of his bag for him. “I like your blouse today,” she said as he was getting undressed.
He wasn’t sure how to answer. “Thanks,” he replied.
“It could use a bit of padding in the breasts though.”
Ugh! Once again he was sorry he had worn it. “I know,” he replied.
She looked up at him as he was pulling his pants off. “Then why didn’t you pad them?”
He shook his head. “I was at work before I found out.”
“You found out at work?”
He blushed. “Yeah, from one of the women I work with.”
“What did she say?”
He shook his head. “I’d rather not talk about it.”
She shrugged her shoulders. “I was just asking. By the way, I’m glad you finally added some color to your face. It looks much better.”
He didn’t want to tell her that it was because of Robin that he had done it. “Thanks,” he replied simply. He suddenly felt the need to pee again. It would be better to do it now than after she had changed him.
She saw him stop undressing for a moment and just stand there. “What’s wrong?”
“I’m wetting myself again. Better now than later.” Cassie laughed.
A few minutest later, Chad was once again sucking on the baby bottle while Cassie was rubbing baby lotion all too intimately into the front of his private areas. She watched him closely. He was staring at her. Even with the bottle in his mouth she could tell there was a worried look on his face. His chastity device prevented her from really touching him where she needed to, but she did her best to excite him anyway. His bottle was half-finished when she finally smiled and pulled her hands away. He had never stopped staring at her. He had never stopped sucking on his bottle. And he had never even begun to get hard. “You’re definitely getting a lot better,” she said. He said nothing, but she thought she saw him blush a bit.
She remembered all too well how he had reacted last night when they had played with her little toy in his asshole. He had done amazingly well then too. Her voice was almost a whisper. “Would you like me to play with your backside a bit again?”
He didn’t know how to answer. Yes he did… but no he didn’t. When she did it, it was the closest thing to a sexual sensation he could feel – other than peeing. But at the same time, it disturbed him way too much. He couldn’t decide.
Her voice was still soft. “You really seemed to like it last night. I don’t have to do it today, I was just wondering.”
She was leaving him a way out. But he had liked it last night. A lot! Without realizing it, he let out a small whimper in his indecision. His need for sexual relief was so much. But the humiliation!
She smiled down at him and took the bottle away from him. “Roll over. I’ll just do it a tiny bit for you, ok?”
He needed it, but he hated it. He despised the fact that it should affect him like it did, but he also wanted it. She put her hand on his hip and pushed. He rolled over and brought his knees under him, lifting his rear end high into the air – totally exposed and open to her touch. Again, he whimpered in his need, and frustration, and humiliation.
Cassie lubed her hands again with the baby lotion and began massaging his backside again. Within moments, she could feel him moving almost rhythmically back and forth under her touch, and she hadn’t even gotten to the good part yet. But when she did start to go there, his movements stopped, completely. She touched him lightly there again and saw the quick shock that seemed to run up his spine. She pulled her finger away, then did it again. No shock this time, just acceptance and waiting. She pushed till her fingertip entered him, then she wiggled it. He arched his back and neck at the sensation. She pulled her finger away again and he almost collapsed back into his original position.
Chad closed his eyes and concentrated on her hands. Once again he felt her place her finger, this time ever so lightly against him. He waited patiently wanting more. Very, very slowly, he felt the pressure increasing, till her finger finally slipped in. Then her finger paused. Would she wiggle it again? But now the pressure was increasing. He could feel her finger going deeper inside of him, then deeper still. He unconsciously let out a small moan. Her finger pulled back, but not out, then pushed in again. Then she repeated the motion. Then she did it faster. All of his muscles began to contract. It felt amazing! He wanted more! But suddenly her finger was gone. No! A minute later it was back again pushing deep inside him. Yes! But then it was gone again. Why? He wanted more. But suddenly she was pushing on him.
“Roll over again,” she said softly and kindly.
He felt so frustrated as he rolled back over again onto his back. He accepted the baby bottle again and he put it back to his lips while he felt her diapering him again.
She leaned over him. Her voice was almost a whisper. “You did really well today, didn’t you!” It was at that point that he realized that his chastity device had never hurt him at all. Not one little bit. And during that last part, he hadn’t even thought about it.
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