Friday, July 30, 2010

The Bet - Chapter 27 (Thursday – week 4 Part 1 of 6)

The Bet
by Karen Singer

Chapter 27 (Thursday – week 4 Part 1 of 6)

Bound and tied... Held captive… Completely helpless… Dark disturbing dreams, all with a common theme, played out in his mind all night long. For once, rarely anyway, did the dreams ever stimulate him sexually. That part of him only got a tiny token acknowledgement… as if his body had given up on it – mostly. Yet it did nothing to stem the restlessness of his dreams.
All of his dream emotions finally coalesced into one dream – one dream where he was Mel’s bound, captive slave. All through the dream he yearned for her touch, her attention, her acknowledgment… her love. And all through the dream, all she did was to treat him harsher and harsher, grinding him down further and further. Yet still he yearned for her and constantly strived for her. He continually tried to show her his devotion in whatever limited way he was able. Till finally… she looked down at him… and smiled at him… and reached out her hand for him… and the loud rock music from his pink clock radio blasted every shred of the dream from his being!
He woke up startled, trying desperately to make sense of anything. What had he been dreaming? As usual, he didn’t have a clue. He was being assaulted by the loud music now that threatened to peel the paint off of the walls. He rolled off of his blow-up mattress onto the empty baby bottles on the floor. Ouch! He scrambled to his knees and reached out for the button on the clock radio and quickly turned off the annoying music. And as blessed silence once again filled the room, he stopped right there and stared at his hand. It was free! There was no high-heeled shoe bound to it. He glanced at his other hand as he wiggled his fingers and felt relief washing through him. The shoes were gone from his hands. Sometime during the night, Mel had removed the shoes… and it hadn’t even wakened him. He felt the pain of his aching feet that were still strapped into the highest heels that he owned, and wished she had removed those shoes too.
Still on his knees, he took time to take stock of his situation. The breast forms glued to his chest under his baby-doll nightly still seemed to be just as tightly glued as ever. His fingernails were still incredibly long and polished a bright red. As usual, his diapers were unbelievably bloated, like a huge basketball… or more likely a bowling ball – because they were so heavy. He could tell that once again he was messy inside of them and not just wet. Again he didn’t remember doing that during the night. His diaper rash was obviously still there too, but was it any better today? He couldn’t tell yet. One thing he couldn’t feel as much, was his penis, totally encased inside the damn chastity device she had locked onto him. He couldn’t feel it, mostly because the device wasn’t hurting him this morning – a blessed relief! And finally, the high heeled shoes Mel had strapped to his feet last night were causing his feet to ache terribly.
First things first! He sat down on his blowup mattress and unstrapped the shoes, wiggling his toes and bending each foot in relief as he did so. Only then did he climb to his feet. It felt good to stand flat-footed again. She wouldn’t really try to train him so that he could only wear high heels? Would she? Damn! He knew without a doubt that she would do it… if she wanted to! It had been only a tiny little piece of some of his fantasies, yet it was a fantasy. And as such, the idea affected him. And as she had said last night, how many of his fantasies had she already brought to the realm of reality? A frightening number of them! And then some!
Taking a deep breath to steady himself against whatever the day might hold for him, he began making his way out to his kitchen to see if she had left him a note. His overly bloated and messy diapers caused him to waddle with an extreme wide legged gait all the way. Her note was there, but it was strange – sort of. There was nothing out of the ordinary at all, and obviously even she had realized it.


You know the rules. You know what you have to do – what you can do, and what you can’t do! See you for breakfast.

What a waste of time! Yet he was very glad too, because she had bothered to write it. Nothing new! For once, everything was normal… if you could call anything about his life “normal.” He waddled over to his refrigerator and pulled out the first of three baby bottles of her nasty tea that he would have to drink before he left for the morning. The bottle had tape wrapped around the top, sealing it so that he would have to drink it like the big baby that he was. He never even gave it a moment’s thought as he carried it out to his sole chair and sat in it. He raised the bottle to his lips and finally realized he was sucking on his pacifier. When had that gotten into his mouth? When he finished his bottles last night, he hadn’t been able to pick the thing up, even though he had tried. Mel. She must have given it to him when she removed the shoes from his hands last night. He mentally thanked her as he took his first sip from his bottle. But the thought of thanking her also sent a tiny bit of fuel to his overly unrelieved sexual feelings once again. Imagine – thanking her for giving him his pacifier to suck on. Damn he needed some relief!

Mel stared at the coffee dripping from the coffee maker into the pot. As usual, it was dripping all too slowly. Maybe she should invest again in a coffee maker that she could set up to automatically come on every morning. There were a ton of them on the market. She had owned several of them in the past. Money certainly wasn’t a problem. She sighed slightly as the coffee continued to drip. The problem was her! She wasn’t disciplined enough to set the darn thing up every night before she went to bed.
But now there was Sissy! He could do it for her. He could set it up as part of his mandatory duties every night. She smiled as she reached for a cup to pour the freshly brewed coffee into. In her mind she was seeing Sissy bringing her coffee in bed, waking her up with it every morning. Sissy! Her dream. And she had just found another way he could be even more useful. Just thinking about him, not to mention what she had done with him last night, brought feelings of joy to her whole body. But those feelings of joy were nothing compared to the feelings she had enjoyed last night. Wow she had been horny! What a night!
As she took her first sip of coffee, the pleasure of the liquid brought images to her mind of the pleasures she had enjoyed last night. Yes, she had had a good time… scratch that… make that a great time! And he had been so funny trying to push the vacuum cleaner with those stupid shoes taped to his hands. She’d have to remember that for the future.
But today was today… another day. It was Thursday. Tonight they had another appointment with Gloria where he would get even more of her hypnotic conditioning. By the way she figured things were going, it wouldn’t take much more at all till he was totally without control – and therefore – hers! She took another sip of her coffee. Mmmm! Sissy had lost! And he didn’t even know it yet!

Chad stared at the clothes in his closet for a moment. Usually they were carefully divided up by type of item, with all the pants in one place, all the blouses together, and all the skirts and dresses in their places. It was still a shock to him to open his closet and not see one piece of male clothing. But this morning, everything looked so different. Since Mel had rearranged things last night, there were skirts mixed in among his blouses. There was something about that that bothered his sense of organization – but what Mel had done for him was necessary – for now at least. He had a hard enough time figuring out what to wear every day. Her efforts were really a big help.
There was no question about what he would be wearing to work today. He had spent yesterday in a skirt and would have to wear a skirt to work tomorrow too. Today he would be wearing pants again… for the last time this week. Technically, there was one other pair of slacks in his closet, but they were a much longer length, and because of his now shrunken waistline, they were pretty much unwearable now - unfortunately.
He had already dressed himself in his usual two diapers, plastic panties, waist cincher, and all-in-one girdle. Today, for the first time, he left the pantyhose off. Trying to put them on while wearing the waist cincher had been too much of a chore. Mel had said he could do without them, at least for work – so he was doing without. It had been a long time since he had gotten dressed without wearing pantyhose. The slacks immediately felt strange as he pulled them up his legs. As he expected, they hung lower on his hips than he would have liked. He grabbed a top that he hadn’t worn before but he was sure would go with the slacks he had put on. The stretchy top fit tighter than he was happy about over his new breasts and stomach, but when he looked at it in the mirror, he didn’t think it looked too bad at all – kind of sexy in fact… if you could call anything about him sexy. Which he wasn’t! Still, for a moment, he enjoyed the sight of himself in the mirror. Damn! Was he really doing this? Going to work… in fact, living his life – dressed entirely as a woman? All the time? Unbelievably, the answer was yes! Damn!
His appearance needed something – like makeup, and his hair done, not to mention his jewelry. Time to get busy getting ready again.

Mel turned sideways as she continued to stare at her reflection in the mirror. She put her hands against her stomach and pushed slightly. Had he called her fat last night? He had said that he didn’t, but she wasn’t totally sure. Why would he ever think that she had worn a waist cincher before? She hadn’t! Ever! She continued to stare at herself and appraise herself. No, she wasn’t fat at all! Ok, so there was a bit of puffiness in her tummy, but it wasn’t that bad. Was that what he had seen? Or had he really not called her fat at all like he claimed?
She wasn’t a spring chicken anymore – not like the Robin woman probably was. But she wasn’t all that old either. Twenty-six wasn’t old? Was it? And yes, she supposed she did need to be exercising more. And ok, her arms were a tiny bit flabby underneath and could use some toning up. But there really wasn’t that much time in her day. She was a professional woman. She was too busy to be exercising all the time. But was she fat? Not as far as she could see! Ok, in her own opinion, she didn’t think she was.
As she grabbed her panties to put on, she wondered if it was worth asking Andrea about… or maybe Gloria… or Cassie. No! Not Cassie. Cassie would immediately try to sell her a gym membership that she didn’t have time for. Maybe just Andrea. Yeah, that would be ok… maybe.
Instead of putting on the skirt-suit she had selected, she put it back into the closet and pulled out her most slimming dress instead. And when she buckled the belt around her waist, she pulled it extra tight! No, she wasn’t fat! Not a bit! She ought to make Sissy eat twice as many meals of baby food for a while just for suggesting such a thing. That would probably teach him a lesson. Suggesting that she was fat! Ha! If he really had suggested it, that is.

Chad rang her doorbell right on time and Mel opened it with a smile on her face. “Good morning, Mistress,” he said as he dropped his usual curtsey.
“Good morning, Sissy,” Mel returned as she stood back to let him in. She watched as he dropped his bags under the table by the door. She took the bag full of empty bottles from him, but she didn’t bother to open it. She was more concerned with looking him over. Did he have to wear such a tight fitting blouse today? Since he had lost so much weight, and with the waist cincher too, his improving figure was becoming more and more noticeable. Did he wear that top just to emphasize how he looked now and to point out that she was getting fat? Ok, the thought itself was ridiculous. So why was she thinking it? Besides, his figure wasn’t that great!
Not wanting to dwell on something that she knew she was erroneously stressing over, she purposely turned away from him so she wouldn’t keep staring at him. “Ok, Sissy,” she said. “Breakfast time.” She purposefully walked ahead of him so she wouldn’t have to look at him and be reminded any further of the weight he had lost. But as she headed for the kitchen drawer to get his bib, she couldn’t help thinking – his figure wasn’t better than hers? Was it? No, that was a dumb thought. There was still no doubt at all that underneath the clothes and the hair and the makeup, Sissy was a man!
Chad pulled the tray off of his highchair, climbed up into it, and pulled the tray back in place. He hated his baby-food breakfasts. They were not only very demeaning, but they tasted awful. He held still for Mel as she tied the bib around his neck. Damn! Just like a baby. And worse, because she made him eat with that stupid baby spoon, he knew he needed the bib – like a baby!
As she walked away, he noticed her turning her head to look at him. Was there something about the look on her face that suggested she was angry with him? If she was, he had no clue as to why. He must have just imagined it.
Mel carried his bowl of baby cereal over to him and felt a tiny bit of relief as she did so. With his bib in place, she could no longer see his breasts sticking out under that tight top he was wearing. And in the highchair, the illusion of him as a baby was far more complete. Much more satisfying today than usual. She smiled at him now as she sipped her coffee and watched him struggling with his cereal. Plop! There went another tiny bit of cereal, off of his spoon, onto his chin, only to run down and fall on his bib. Delightful!

Tuesday, July 27, 2010

The Bet - Chapter 26 (Wednesday – week 4 Part 6 of 6)

The Bet
by Karen Singer

Chapter 26 (Wednesday – week 4 Part 6 of 6)

Mel watched him, totally delighted with what she was seeing. Obviously, he was having a lot of trouble with such a simple task. And just as obviously, he was quickly learning how difficult the simplest tasks could become with heels on. Ok, so it wasn’t really a fair test, but the whole purpose was for her amusement anyway – and she did find it amusing – very!
It took a long time for him to just finish vacuuming her bedroom, and by the time he was done, she couldn’t stand it anymore. Before he could drag the machine out of her room, she herself reached down and turned the thing off. Then, grabbing him by the wrist of one of his high-heeled covered hands, she dragged him out into the living room and stood him in front of her sofa. She quickly went to her desk drawer where she dragged out the ropes she used to tie him with.
Chad was a bit shocked to see her dragging the ropes out again, although he knew he shouldn’t be that surprised. What he didn’t expect was for her to tie his shoe-covered hands behind his back before she even undressed him. But she seemed to suddenly be in a huge hurry. And when she pushed him down to his knees, still completely dressed, he was more surprised than ever. Very quickly, she had him spread his knees for balance, then she tied his ankles together. But she still wasn’t finished. She tied one more rope to his bound wrists and then wrapped the other end of the rope to his bound ankles. Pulling tightly, she pulled his body backwards, bending him back toward his bound ankles. His arms were stretched back torturously, keeping him very off balance. He was still on his knees, but staying upright wasn’t as easy. If his knees hadn’t been spread, he would have fallen over for sure.
Mel suddenly left him there and he had a few moments to reflect on his position, which was uncomfortable to say the least. She was back a few moments later though and his sight was quickly taken away as she tied one of her scarves tightly around his head. He knew what was about to happen, but he was a bit apprehensive about it. There was an urgency in Mel that he didn’t see very often. He was suddenly a bit afraid of the task he was about to have to perform.
Mel glanced down at her captive sissy maid. She had tied him tighter than usual, and doing so had gotten her juices really flowing. She felt more excited tonight than ever before! Seeing him in his maids dress tonight, all trussed up and helpless seemed to make things that much more exciting for her. He was her fantasy – her perfect maid! Even though that fantasy had seemed to change a bit over the past month. It was now a better fantasy than ever! And it was also now a reality!
She hated taking the time to run to the bathroom to get some towels to protect her sofa, but she knew better than to do this without them. As quickly as she could, she spread them out. Finally, she was ready.
She looked down at him. He was bent backwards, trying to take the strain off of his arms – it wasn’t working. She reached down and caressed his face lovingly. “You know what comes next?” she asked in a rather soft, sultry voice.
Chad gulped apprehensively. But he did know. He was about to have his face shoved roughly into her wet and waiting sex. “Yes, Mistress,” he answered.
She chuckled lightly. Checking once again to make sure he couldn’t see her, she took off her blouse and draped it playfully over his bound arms. She lightly rubbed her bare stomach over his face… ever so lightly. She removed her bra and draped that over his bound arms too. Then she grabbed his face in her hands and rubbed the smooth, soft skin of her breasts back and forth against his face. Over and over again. Exciting her. Teasing him with the feel of them.
She kicked her shoes off quickly and slid out of her slacks. As she tossed them aside, she noticed how obviously wet her panties were. It was a good thing that he was blindfolded and couldn’t see them. She grabbed his face again and spread her legs to either side of him, pulling his face into her wet, panty-covered crotch. She ground that crotch into his face for a few moments before releasing him and moving away. She was so worked up tonight. She didn’t know why and didn’t really care.
She quickly pulled her panties off, almost tearing them in the process and sat down in front of him on the towels that were protecting her couch. She grabbed his head roughly and pulled him toward her, rocking him on his knees, pulling him from leaning backwards to falling forward – directly into her wet and waiting sex. She felt the panic in his body as she pulled him forward and vaguely saw his raised feet off the ground, but in truth, she didn’t care about his discomfort. This time… this moment… was about her and her needs. Not his. She was his mistress and he knew it. Her needs were raging!

Chad fought the position he was in, but there was nothing he could do about it. Tied as he was, there was no escaping the gravity that pulled his face into her waiting crotch. And what a wet, messy crotch it was. Being unable to move his head and body anywhere else, he soon found himself fighting for air as she forced him to grind his face against her sex. She was using him hard already. He tried to do what he could with his tongue, but she was too demanding of him, pulling him too hard, too fast for him to do anything but let her have her way with him.
He felt her orgasm, then as soon as it was done she was pulling at him harder still, wanting more than she had before! She was all need and nothing else. Again he felt her orgasm, and again she began grinding against his battered face like never before. It wasn’t till after her third bout of ecstasy that she finally slowed down, almost seeming to luxuriate in the sensual pleasures of his face against her love spot. Chad took the few seconds of her slowed pace to try to catch his breath and also to wrinkle his nose to relieve the feelings of total abuse that had been wrought against it. What had gotten into her tonight? She had never been like this before?
Since her pace had finally slowed, and he could now breath again… and since she still didn’t seem to want to stop, he tried once again to reach out with his tongue into her very soaked sexual organ. He felt her shudder clear through to his own toes.

Mel breathed in deeply. Her eyes were closed – they had been for quite a while now. She concentrated on the feelings now coming from his talented little tongue. Marvelous! Marvelous! Marvelous! This was life. This was living. This was really what it was all about! All the rest of life was simply waiting, marking time, for this!
Now that she felt more satisfied, the feelings were building slower than they had before. They were more subtle, and as such, more interesting. She could relish in just feeling, and concentrating on, and appreciating – each and every variation of each and every sensation. Glorious… glorious!
It was slower and not as earthshaking, but still her next orgasm was one to appreciate and savor for as long as she could maintain it. Then, on the way down, her body was forced to catch its breath. Yet she didn’t let up on the sissy in her lap. She kept him there, forcing him to give her pleasure… pleasure beyond pleasure.
She felt his tongue slowing, tiring, yet she had no sympathy for him. Her final orgasm came much like the first… building ever so gradually, then staying at the peak for a very long time, then finally diminishing all too quickly. Only when she realized that she was finally done, did she open her eyes and push him backwards… back so that he was leaning backwards once again.
She stared at him. He looked awful… about as bad as she felt good. She felt so satisfied. Yet part of that satisfaction came from the knowledge that he couldn’t get any satisfaction at all. That was a huge part of the allure for her – knowing that she was denying him the very male birthright that he probably valued the most. Yet as she stared at him, there were other emotions in her gaze. Emotions she wasn’t ready yet to recognize… other than perhaps – fondness.
She got up and leaned down next to his side, putting her hands on him. “Here,” she said, “let me help you lay down.” Tenderly, she laid him on his side. She leaned down and kissed his sex soaked head. “I’ll be back in a bit,” she whispered. She stood up and headed to her bathroom for a much needed shower.
Chad laid on his side, blindfolded and tied uncomfortably, still dressed in his maid’s dress, his hands still encased in the high-heeled shoes she had taped onto him, his entire head soaked with the essence of her sex. He could hardly move. He was just glad it was all over. Now if she would just release him soon he’d be a lot happier. He took the time to try to relax as much as he could, but the way she had him tied was putting too much strain on his arms and shoulders.
She had been a terror tonight. Beyond anything she had ever shown before. Yet the fact that he had been able to please her that much, pleased him. He felt good about it, as if he had managed to accomplish something extra good. So why couldn’t she be kind enough to untie him now? Damn! At least she could remove the blindfold so he could see again!
Mel dried herself off after her shower and belted her robe tightly around her. She had left him out there, all tied up, for quite a while now. But she had no intention of letting him loose just yet. A few more minutes wouldn’t hurt him. She wandered back out to her living room and checked on him. As she expected, he hadn’t moved an inch. She saw him move his head a bit at her approach. She ignored him.
She walked around picking up her clothes and the towels that had been protecting her furniture, then she took them all into the bathroom to throw them into the hamper. From there, she went into her bedroom to prepare for what she needed to do next.
Chad mentally screamed when he heard her walking off. Why wasn’t she untying him? His arms and shoulder ached – damn it! But he remained silent as he laid messy and exhausted on her living room carpet. It was a little while later when he finally felt her coming back… actually he never heard her coming, he just suddenly realized she was next to him. She didn’t say a word as she began untying him. The ache in his arms and shoulders was suddenly much worse the moment the rope binding his arms back to his ankles was released. He wished he could stretch and rub them, but that much was still impossible. He felt her releasing his ankles, more new freedom. He waited for her to untie his wrists… but she didn’t.
“Stand up,” she prompted softly as she pulled up gently on his arm.
With her help, he worked his way to his feet and he let her lead him wherever she wanted him to go – into her bedroom he supposed. Finally, he felt her working on the ropes that bound his wrists together… and finally he felt the freedom that his arms craved. He moved them around a bit, trying to get the circulation going again and relieve the awful aching that had built up in his shoulders. He tried to rub them, but the shoes that were still taped to his hands felt strange and hard against his skin. He accidently poked himself with one of the heels as he attempted it. He didn’t dare try that again.
He waited for her to remove his blindfold… or even the shoes taped onto his hands, but instead he felt her loosening the apron tied around his waist that was part of his maid’s uniform. A minute later, she was unzipping his dress and pulling it off of his shoulders, guiding it down his arms and over the shoes on his hands. He stepped out of it as he felt it pooling on the floor past his legs.
She removed the shoes from his feet. His pantyhose and girdle came next. What a relief it was when they were off. Then she attacked his waist cincher… the relief was twice as great. He tried to rub his stomach for a moment, but again, the shoes on his hands felt too strange. Finally, she removed the plastic panties that added the extra protection he needed against his diapers leaking. She had stripped him of almost everything, except the blindfold and the shoes still taped to his hands… and of course his diapers.
She led him gently over to the bed and helped him climb up. A moment later, he felt her removing his sodden diapers, the cool air felt strange and oddly erotic against his bare skin there as soon as they were gone. The wet washcloth she used to wipe him up with felt wonderful too. Very wonderful!
“Roll over, Sweetie,” she said softly as she pushed gently against his side. He rolled over onto his stomach. She wiped his backside more thoroughly with her washcloth. “Your diaper rash is looking better,” she noted. She placed her hand under his stomach. “Hands and knees now, Baby.”
Chad pulled his knees up under him, but when he tried to brace himself on his hands, he found it next to impossible because of the heels still attached to them. No matter how he placed them, he just couldn’t find a suitable position to fully take his weight and brace himself for what he knew was coming. He heard Mel chuckling softly at his predicament. He finally wound up dropping down onto his elbows with his shoe covered hands out of the way. The position left his backside all too exposed up in the air, but he figured that was what she really wanted anyway.
“Here it comes, Baby,” he heard her say. He suddenly felt the hard cold point of her toy up against his asshole. He felt her pushing on it. “Open up, Baby. Let it in.”
And he did. He relaxed and opened up, because he wanted to let it in. He wanted to feel all the delicious sensations that it brought him. The only wonderful sensations he could feel anymore. The sensations that were now the closest thing to sex that he was capable of feeling.
But once she had worked it in and out a few times, loosening him up, getting him used to it, getting him to the point where he was wanting more and more from it, she began working her toy differently than before… almost more purposefully. Over and over again, despite how he wanted her to push it, she was angling it down, pressing with it against the same area over and over again. Within moments, he felt himself suddenly needing to release some fluid… but not quite like peeing. And there was no stopping it. “Good baby,” she crooned as soon as he felt the fluid leaking out of him – more and more with each stroke that she made with her toy. She was milking him again. Purposefully. And there was nothing he could do to stop it.
When she saw no more of his milky seamen dripping out of him, she pulled her dildo completely out of him, granting him no real pleasure at all. “Well, that job went easier than I thought it would,” she exclaimed.
He just sighed and buried his head in his arms.
A thick coat of diaper rash cream, one suppository, three layers of diapers, and plastic panties, and he was done. Finally, she removed his blindfold and washed his face with her washcloth. He felt better… much better. Now if she would just remove the shoes that were taped to his hands… But instead, she went out to the living room and brought back his highest pair of heels. She herself strapped them onto his feet for him. “Ok, Baby. Let’s go back to your place and have a look at your wardrobe.”
That fast, she had changed the mood… not to mention the subject.

Chad felt incredibly stupid, even in his own apartment, walking around with the stupid heels taped to his hands. They made his hands useless… well, next to useless anyway. There wasn’t much he could really do with them like they were. Fortunately, Mel was handling most of what needed to be done… if it involved hands anyway.
Now she was in his closet, pulling out blouse after blouse and holding them up against one of his skirts that she held in her other hand. “See, these all go together perfectly,” she explained. Actually, Chad was only partially understanding everything she said. But he acted like he was understanding it all anyway. At least when she was done with each skirt, she placed it back in the closet right next to a couple of blouses that she thought would go best with it. As far as Chad could tell, once again it looked like everything went well with everything else, and it was just a case of what your personal style was. Basically though, he was just glad to have some outfits sorted out for him.
As she was finishing with the last skirt, he remembered another question he had for her. “Mistress,” he started tentatively, “would it be ok if I didn’t wear pantyhose? With the waist cincher, they’re almost impossible to get on. How do you manage it?”
Mel laughed. “I’ve never worn a waist cincher!” she replied. Then she got a more angry look on her face. “Are you saying that I’m fat?”
Chad was aghast. “No! Not at all! Of course you’re not fat! I just wondered, that’s all. I thought you might have worn one before.”
Mel looked a little less angry, but only a little. “If you don’t want to wear them to work, that’s your decision. But whenever you’re in uniform pantyhose, or some kind of hose, are required! Got it?”
“Yes, Mistress,” he said dropping a quick curtsey.
“If it thrills you enough, as I suppose it probably does, you can get yourself some stockings and a garter belt to hold them.”
Chad was surprised at her suggestion. It did have a certain allure. “Thank you, Mistress.”
“And you better not be telling me that I’m fat!” she exclaimed once again as she closed his closet door.
Chad knew he was on thin ice. He hadn’t said she was fat… not at all! One thing that anybody could easily tell, Mel was not fat! She was… perfect!
Mel grabbed his baby-doll nighty and pulled it over his head. “Ok, Sissy. To bed with you. I’ll get your bottles for you.”
Chad couldn’t believe it. She wasn’t going to remove the shoes that were taped to his hands – let alone the shoes strapped to his feet. He held them out. “Mistress, are you going to remove them?”
She smiled. “No. They amuse me. Leave them.”
“How about my other shoes,” he asked, indicating the heels on his feet.
“They amuse me too,” she replied with a wicked smile.
With a big sigh of frustration, Chad made his way to his blowup mattress and laid down while Mel went out to the kitchen to get his nightly bottles. The shoes covering his hands made it impossible to pull the covers over himself properly. When she came back, she set both bottles along with his pacifier down on the floor next to him and pulled the covers up for him. “What am I supposed to do in the morning?” he asked as he held up his shoe covered hands again.
She chuckled lightly once again and her wicked smile returned. “We’ll just have to see, won’t we!” Then she held out one of the bottles for him to take.
Chad had a lot of trouble holding the bottles with the shoes on his hands. But once squeezed in place between them, he was able to lay there and drink it easily. Mel watched him to make sure he could manage well enough, then she walked over to his bedroom door and turned out the light at the switch. “Good night, Baby. Sleep tight.” And with another wicked smile, she was gone.
Chad laid there in the darkening room, wondering what he was going to do in the morning. He couldn’t manage anything with his hands handicapped the way they were. He couldn’t even phone her to ask for her help.
The heels still on his feet began to ache. He wanted desperately to remove them so he could flex his feet. But that was impossible because of the heels strapped to his hands. Impossible! Impossible! Impossible! His whole situation was impossible! His whole life was impossible! And that’s what he mostly thought about while he drank his entire first bottle, and his entire second bottle. He desperately wanted the pacifier she had placed on the floor next to him but he couldn’t pick it up to put it in his mouth. Feeling very frustrated, he finally fell asleep.

Late, late that night, Mel snuck quietly into his room as she did every night. He was such a sound sleeper that it would take a lot to wake him. She quickly set the alarm on his pink clock radio so he would wake up when he needed to. She knelt down next to him with the scissors she had brought and cut the tape that bound the shoes onto his hands. She slipped the shoes off as gently as she could so as not to wake him. He stirred, but didn’t fully come awake. Good. She saw him moving his lips and tongue a bit restlessly. She took a chance and picked up his pacifier from the floor that he obviously hadn’t been able to pick up earlier. She touched it to his lips and watched as he instantly took it in and began sucking on it. His restlessness suddenly ceased and he fell back into a deeper sleep. She leaned over and kissed his forehead with the barest graze of a kiss. “Sleep well, my baby,” she whispered ever so softly. “Sleep well.”

Friday, July 23, 2010

The Bet - Chapter 26 (Wednesday – week 4 Part 5 of 6)

The Bet
by Karen Singer

Chapter 26 (Wednesday – week 4 Part 5 of 6)

A little while later, Chad had the kitchen totally cleaned to his satisfaction. But would it be good enough for Mel? She had never complained about his work before. In fact, the only comments she had ever made were about how good it was. As he looked around the kitchen, he didn’t expect to hear any bad comments from her at all.
He walked out to her living room where she was sitting staring at the computer in her lap. He dropped his usual curtsey. “Mistress, I’ve finished in the kitchen.”
She looked up at him, but she was a bit busy just then. “Find something to do then. Clean, laundry… just get to work on something. I’m a bit busy right now.”
“Yes, Mistress,” he replied, noticing that she was already back to concentrating on her work again.
As he headed for her laundry hamper in the bathroom, he heard her calling behind him, “Remember, only my laundry. None of yours!”
“Yes, Mistress.”
It took a little while, but Mel finally finished what she was working on. She didn’t usually mind bringing so much work home with her, it went along with the territory for having a high-paying career. It especially didn’t bother her much because she was single. But there were times lately when she’d really rather be doing other things. Things that were far more pleasurable.
But now the work she absolutely had to get done tonight was all finished. It was time to move into more “fun” areas. She looked over at Sissy. He was putting more wash into the washer. Now how could she have a bit more “fun” with him? She got up from her seat and sauntered over to where he was working. “Tell me, Sissy,” she said as he was stuffing the washer, “have you given any more thought as to if you’d really like me to train you so that you could only wear high heels and nothing but high heels? Have you thought about it at all?”
Chad was flabbergasted by her question. Yes he had thought about it. It was one of those little fantasies that had been fueling his horribly unsatisfied sexual need lately… mostly because she herself had been threatening him with it. Was she going to really do it? The very thought of it sent a small shudder throughout him… while at the same time, the very thought of it stimulated him greatly. No way to win! “Uh… Yes Mistress, I have thought about it.”
“Well, what do you think? Do you really want it?”
What kind of game was she playing tonight? Yes he did… but also, no he didn’t. While it would be horribly humiliating, he had no doubt it would also be a major pain – literally. But how should he answer? “Um… I think that should be up to you, Mistress,” he finally replied.
Mel considered his answer, then nodded her approval. “Good answer. Because it is up to me - and only me.” She watched him as he finished putting the clothes in the washer. “But I still haven’t decided yet,” she replied as if she barely cared.
Chad poured the detergent into the washer and closed the door. Then he turned to face her. “As I said, it’s completely up to you.”
“Yes it is,” Mel agreed again. She stood there staring at him for a few moments, then she put a wicked smile on her face. “Maybe we should kind of ‘try it out’ for a little while… to see how it might be.”
“Try it out?” Chad wasn’t at all sure what she was talking about, but he was suddenly very wary.
“Yes. I think that’s exactly what we should do. Tell you what, go home and bring back three or four pairs of your highest heels.” As she stood there looking at him, Chad wasn’t moving at all. Instead, he just had the most quizzical expression on his face as if he didn’t understand at all. “Well get going!” she ordered. “Get some heels and bring them back here. Now!”
Chad blinked several times as if trying to come out of a trance, then he almost ran for his purse by the door to grab his keys. Why did he need so many shoes? What did she have in mind? As he raced out her door, and even though he had worn heels an awful lot lately, he realized that tonight she suddenly seemed to be covering all new territory. But exactly what territory was that?
Mel chuckled as she watched him hurrying out. It was only a tiny idea, but the more she thought about it, the more excited she was getting. If she didn’t watch herself, she’d have to change her panties before long.
Chad hurried into his apartment and then into his closet. Three or four pairs of his highest heels? As he knelt down and compared all his different shoes… of which he realized he had quite a few… the thoughts of Mel training him so that he could wear only high heels and nothing else ran through his mind. Once again he cursed his predicament where he couldn’t get any sexual relief at all. It was becoming too much. She was doing this… fueling his fantasies… purposely! One thing was for sure, she really knew how to tease him and push his buttons.
He grabbed two pairs of shoes in each hand and hurried back to Mel’s apartment. When he got there, he found her sitting in her living room once again, waiting for him. He dropped an awkward, quick curtsey as he stood in front of her and held all the shoes out so she could see. “I brought these,” he said.
Mel looked carefully at all the shoes in his hand. “Put them all on the coffee table so I can see them better.” She already knew every pair of shoes that he owned, but this was all part of her game. Yes, they were definitely all his highest heels, even though two pairs had the same heel height and were a bit shorter than the rest. She selected an open toed pair of sandals that had the highest, slimmest heel. He had been forced to wear them to work lately with his longer slacks. “Put these on, for now. ”
Chad picked up the pair of shoes she had indicated and sat down in another chair to put them on. He kicked off the comfortable pair of low heeled shoes he had been wearing and grabbed the right shoe.
“Wait a minute,” she interrupted. We want to test the difference… to see which would be better for you, high heels, or low. Just put the left heel on, then keep your regular shoe on your right foot.”
Chad gasped in surprise. “What?” What she had said made no sense.
“You heard me. Put the high heel on your left foot and keep the low heel on your right foot.”
“Are you going to argue with me? Because I can certainly arrange to beat you black and blue instead!”
“No, Mistress,” Chad replied hurriedly. He was still a bit bewildered by it all, but he quickly grabbed the left high heel and strapped it onto his foot, then he grabbed his right low heel and slipped that back on.
“Now get back to work,” Mel ordered.
Chad stood up again. Immediately he felt the awkwardness of having two drastically different heel heights on his feet. As he walked back toward the washer area, he realized just how awkwardly – and clunkily – he was walking. But there wasn’t any other way to move. He was totally off balance, not to mention uncomfortable. What kind of weird game was this? He hoped the dryer would finish soon so he could just stand still and fold clothes – slowly.
Mel almost burst out laughing as she watched him trying to deal with the two different heel heights. It “sort-of” gave him a slight limp as he walked – but really, it was more just an odd awkwardness. “I think the furniture needs dusting,” she prompted, trying to suggest an activity that would keep him walking around the room.
Chad wasn’t at all pleased with Mel’s suggested activity, but what choice did he have? He clunked his way over to get the dusting materials and started in on the table next to the door.
Mel had to get up from her seat to watch him working. But really, she was enjoying his plight so much that she couldn’t have sat through it anyway… at least not very long. Every time he had to take a few steps somewhere, she saw him turn and look at her. Each time, it looked like his face was getting redder and redder from embarrassment.
Chad moved on to the next end table. As he did so, he glanced quickly at Mel. She was certainly enjoying herself, watching him trying to walk in two different shoes. Dumb! The more he had to keep walking, the more difficult it seemed to get and the sillier he felt about it. His feet were getting tired too. With the two different shoes on his feet, there was no doubt as to which pair was the more comfortable – the low-heeled shoes for sure! It wasn’t long at all before he was wishing to have both of the low-heeled shoes on his feet once again. The high heels might be fun for a little while, but trying to do it like this was ridiculous!
Mel watched as Chad finished dusting the lamp on one of the end tables. He had been wearing the two different shoes for a while now. It was time to change things up a bit. “Ok, Sissy, let’s try something different.”
Chad was immediately afraid of anything she might suggest, but he held his silence and waited.
“Change feet,” Mel ordered.
“Put the high heel on your right foot instead and then put the low heel on your left foot.”
Ugh! Chad couldn’t believe it. Now she wanted to do the same thing, just switching feet. Having no choice though, he dutifully grabbed the shoes he needed and strapped the high heel onto his right foot and slipped the more comfortable low heel onto his left foot. Immediately he felt the sense of relief on his left foot as he slipped the low heel shoe on. Standing up also brought a sense of relief to his left foot… but it brought a feeling of extreme awkwardness to his right foot – not to mention a lot less comfort. He had just started to get used to having the heels the other way, now he had to switch things up and was once again feeling more off-kilter than ever.
“Vacuum the carpets,” Mel ordered, suggesting something that she knew would keep him on his feet and moving.
“Ugh!” was Chad’s only silent thought. Pushing the vacuum cleaner around was hard enough, but with the two different heels on his feet, the job was twice as hard, and twice as tiring. He was aware of Mel constantly watching him… and constantly laughing at him all the time.
“Are you enjoying the different shoes?” she asked at one point.
Chad searched for an answer, but he really couldn’t come up with one. Yes he was enjoying it… sort of, but at the same time, it was awkward and very uncomfortable. And she was laughing at him the whole time.
“How do you find the two different shoes?” Mel finally asked.
Chad stopped what he was doing and turned off the vacuum cleaner so he could talk. “I’m really starting to appreciate the low heeled shoes a lot more now,” he replied. I always knew they were very comfortable, but when you compare them to the higher heels at the same time… there’s really no comparison.”
Mel smiled wickedly at his answer. “So are you still fantasizing about me training you so you can’t wear anything but high heels anymore?”
Chad shrugged. “I haven’t had time to consider it again. But I guess so. It was just a dumb fantasy.”
“But how many of your dumb fantasies have I brought to life now?”
Chad only thought about that for a moment. “All too many,” he replied with a bit of fright. Was she really going to do this to him now? Add another humiliation on top of everything else? Would she? He had no doubt at all that she really would… if she wanted to.
“Ok, Sissy. Change up time again.”
Huh? Now what?
“Grab another pair of heels and put them on. Both feet this time.”
Chad shouted a mental hooray! Finally, he could at least walk better! He quickly grabbed another pair of shoes and strapped them onto his feet. He stood up and had to take a few steps before it felt normal to have the same heel height again. What a pleasure – even if they were high heels.
“Back to work, Sissy,” she ordered.
Chad gladly dug into his vacuuming chore once again. At least having heels the same height made the task a lot easier, even if it was a lot more difficult than trying to do it in low heeled shoes.
But as Mel watched him, she wasn’t getting nearly as much pleasure out of it as she had before. “Hold it, Sissy,” she ordered.
Chad turned the vacuum cleaner off again. Now what?
“Go back to the way we started. Highest heel on your left foot, low heel on your right.”
It was all Chad could do to not scream loudly with frustration! He strapped his highest heel back onto his left foot again and slipped the low heeled shoe back onto his right foot. After having heels the same height for a few minutes, he immediately felt the awkwardness of it again. But this time, he got used to it a lot faster. Once again, he clumped around clumsily as he vacuumed Mel’s apartment.
Mel was enjoying his plight much more now that he was having to deal with the two different heel heights again. But the more she watched him… maids dress, makeup, hair curled, super long red fingernails, and now two different pairs of shoes… not to mention the diapers he was wearing underneath… the more it was starting to get to her. She was absolutely loving it – forcing him to do things that were so far off from what a normal person would do. The more she watched him, the more “drunk” with power she was becoming – not to mention excited.
She could see though that he was quickly becoming used to the two different shoes again. Time to change things up again. But what could she do that would be different? She considered that question as she watched him shoving the vacuum cleaner around her bedroom. It was a stupid idea that hit her, but still, it was a different idea. And… it kind of appealed to her. “Ok, Sissy. Time for something different again.”
Chad turned off the vacuum cleaner so he could hear her better. He was a bit apprehensive, but really, he was now getting used to the two different heel heights so it wasn’t nearly as much of a problem. He fully expected her to have him switch the shoes again like she did before.
Mel led him back out to the living room where she picked up a pair of three inch strap on sandals from the pile on the coffee table. “Here put these on,” she ordered. She could clearly see how surprised he was by her request, but there was a slight look of satisfaction on his face as he sat down to remove the shoes he was wearing and put the new pair on. As soon as he had them strapped in place, she had him stand up and walk over to stand in front of her. “Do those shoes feel good?” she asked.
He smiled. “Yes, Mistress. And it’s certainly a lot easier to walk when both heels are the same height.”
She nodded, “Good. I’m glad it’s easier… because now we’re going to make things harder!” With that, she picked up a pair of three inch heeled pumps from the table and grabbed his left hand. She held up one of the shoes. “Stick your hand in!” she ordered.
Chad’s first instinct was to shy away and pull his hand back as he mentally gulped. But he did as he was told and shoved his hand all the way into the high heel she was holding out. She held the other shoe up for him and he shoved his right hand into it like the first one. He was less sure than ever now of what kind of game she was playing tonight. He felt her tugging slightly on the heels of the shoes as if to pull them off of his hands, then she seemed to reverse herself and push them back onto his hands as hard as she could.
“Push your hands all the way in,” she ordered.
“They are,” Chad replied.
Mel frowned. This wasn’t working like she hoped it would, the shoes weren’t made for his hands and would fall off too easily. “Follow me,” she said as she turned and led the way over to her desk. A minute later, she started wrapping tape around the shoes and his hands – taping them into place so they couldn’t fall off.
Chad was aghast as he watched Mel wrapping layer after layer of tape around the shoes on his hands and then his wrists, making sure that they couldn’t be pulled off. His hands were now totally useless. It also felt odd to have his fingers stretched out straight and locked together inside the shoes. It also felt odd because the fingers were bent backwards a bit due to the curve of the shoe. It wasn’t exactly comfortable, but he had no doubt that his comfort was not exactly on Mel’s list of priorities for the night.
When she had finished, he held his shoe covered hands up in front of him and waved them around a bit, trying to get the feel of them. His hands were totally useless now and there was really no way that he could remove the shoes himself. And because of that, he felt a huge stirring from his ever-present sexual need. Even this was stimulating him enormously!
“Go finish vacuuming now,” Mel ordered.
He looked at her like she was crazy. He had no hands! He couldn’t do anything! “How?” he asked as he waved his shoe covered hands in the air again.
But Mel was almost laughing at him now. “You’ll just have to figure something out.”
Chad stared at Mel for a moment, taking in the wicked grin that never left her face. She was serious! Sort of. He did realize that this was all just a game for her. Actually, he supposed it was all just a game for him too. That thought made him feel a bit better about what was going on. It was all just a game. Everything was all just a game.
Feeling a bit better about it, he turned and went back to her bedroom where the vacuum cleaner was. As he walked, he almost lost his balance because he wasn’t used to the heels on his feet anymore, and with his hands locked away in the shoes, it felt like they were throwing his balance off a bit too. He recovered quickly though and carefully continued on.
He was very aware of Mel leaning against the doorjamb as he stood looking down at her vacuum cleaner. His first problem was figuring out how to turn the darn thing on. Not a big problem. He just pressed the switch with the toe of one of the shoes. But then he had to push the thing… and he had no way to grab it with his hands. He tried to pin the handle between the soles of the two shoes on his hands, but he couldn’t pin it hard enough and when he tried to push it, the slippery soles just slid along the handle and the vacuum cleaner stayed right where it was. He tried doing the same thing with the sides of the shoes instead, but while he finally managed to push it just a bit, it was too hard to manage and he mostly had the same problem.
The darn shoes on his hands made things much more difficult because there wasn’t really a lot of sole on the bottom of them that he could work with. Mostly, just under the toe and that was all. Finally, he placed the bottom of the toe of his right hand against the tip of the handle and locked the heel on his left hand under the handle to steady it and hold it up. And it worked. He heard Mel laughing and clapping for him from her doorway spot.
But pushing a vacuum cleaner forward was only a tiny part of the battle. How was he supposed to pull the darn thing backwards again? Ugh! He tried grabbing the handle by putting both heels around it, but the shoes on his hands just didn’t let him grab it hard enough to let him pull it. Finally, in desperation, he wrapped his elbow around the handle and squeezed with it. It worked, but it wasn’t easy! And through it all, Mel laughed at him. As he once again pushed the cleaner forward a few feet, then reversed his position to pull it back again, he supposed he would be laughing too – if her were in her position.
As he worked, he became more aware of the heels on his feet than ever. Even though they weren’t as high as some pairs that he had worn, the extra difficulty of his task and the fact that he needed to constantly brace himself with his feet was still made that much more difficult because of the heels. His feet sometimes slipped, and if he wasn’t careful, he could easily have broken an ankle each time he didn’t set his feet right. Between the shoes on his hands and the shoes on his feet, he was having a very difficult, tedious time of it.

Tuesday, July 20, 2010

The Bet - Chapter 26 (Wednesday – week 4 Part 4 of 6)

The Bet
by Karen Singer

Chapter 26 (Wednesday – week 4 Part 4 of 6)

It was the middle of the afternoon. Chad had his head buried in his computer screen, reading and rereading what he had already written for Mel. Surprisingly, he had managed to write quite a bit, almost enough already. But the truth was, despite how much he had written, he really hadn’t learned anything. As far as he could tell, you could mix almost anything with anything else. It all depended on what “look” you wanted. He thought quite a bit about his personal “look.” Actually, he wasn’t sure he even had a personal “look” yet. He just did whatever Mel told him to do. Did she want him to develop his own look now? He hoped not. All his research had only confirmed that it wasn’t as simple or as cut and dried as it seemed. However, it did seem interesting… all those different styles of clothes. It really looked like so much fun. As he looked at the many pictures, he often wondered what it would be like to dress and look like so many of those models. The old feeling of jealousy reared its head again because he wasn’t born female and couldn’t ever possibly have a body like they did. Sigh!
“Hey Sissy, it’s break time,” Robin’s voice called from the entrance to his cubicle.
Suddenly panicked, Chad quickly minimized the report he had been writing for Mel so Robin couldn’t see it. Had she seen it? He hoped not. He turned to face her. “I don’t think I want to go right now,” he replied. “I’ve got too much to do.”
“Oh come on. We don’t exactly have a deadline on this stuff. You don’t have to try to get it all done today.”
Chad smiled, more so because it sounded like Robin hadn’t seen what he had been working on for Mel. “Yeah, I know. But sometimes when I’m going good, I don’t want to stop.” It wasn’t exactly the truth, but things did go that way sometimes.
Fortunately, he saw Robin smile in return. “I know what you mean. Have at it then.”
Chad was ever so glad she had agreed this time and wasn’t going to drag him down for more humiliation. He expected her to leave, but she didn’t. Instead, her face suddenly looked quizzical.
“Hey Chad, I heard you doing an awful lot of typing today with those nails of yours. More than I’ve ever heard you type like that before. What’s up?”
Shock and fear ran through him. Of course his nails had made a lot more noise on his keys. He should have realized that Robin would have heard it. “Um…” He searched for an explanation. “Sometimes I have a lot of code to type. Today was one of those days. That’s what I meant when I said I was going good and need to keep at it.” It was a total lie, but it sounded good to him. In fact, it really could have been the truth – under other circumstances.
“Oh, that makes sense,” Robin replied. She smiled and finally said, “See ya’.” And she was gone.
Chad breathed a small sigh of relief as she left. He turned back to his computer and brought up his paper for Mel and started finishing it. Overall, the paper had gone faster than he had expected. He was just glad to be almost done with it now. He was very surprised at how adept he was becoming at typing with his stupid long nails. In fact, it had actually been kind of fun… in a way. Well, different anyway.
As he worked, he suddenly realized that he had to pee yet again. “Geez!” he thought. “It seems like I just went.” As he glanced at his watch to start timing himself again, he thought back through the afternoon. Despite having very little to eat and drink for lunch, as he usually did now, he had been peeing more often. Much more. And as he thought back through the entire day, he realized that he had been peeing more all day. Why? Having no answer, he went back to finishing up his paper for Mel.
It didn’t take him long to finish it, and with a few happy clicks of his mouse, he emailed it to Mel. He leaned back in his chair, happy to be done with it so he could get back to work… not to mention so that he could stop worrying about Robin finding out what he had been doing. The pressure on his bladder was getting fairly intense, but he held on tightly.
“Hey Chad,” Robins voice suddenly interrupted his thoughts.
He looked up to see her standing at the entrance to his cubicle once again.
“We were talking during break, and everyone wants to know what kind diet you’re on. We’re all pretty impressed with how much weight you’ve lost… and so quickly.”
“What diet I’m on?” he asked, horrified at the question. Yes, he had lost a lot of weight since the bet had started, but he couldn’t really explain to Robin why it looked like he had suddenly lost so much more weight. He didn’t want to tell her at all about his waist cincher, or about how most of his meals had been nothing but baby food lately, or about a thousand other things. But he needed an answer. “Um…” he thought for a moment. “Like I said before, it’s really just a lot of basics. Plus I’m not eating as much as I did before.”
“What basics?” Robin asked.
“Well…” Chad thought for a moment. The pressure on his bladder was getting more severe. And then two thoughts hit him at once. The first was an answer to Robin’s question, and the second was that the reason he was peeing more today was probably because of the darn waist cincher pushing against his bladder. He tackled Robin’s question. “I got this new cookbook, all about diet cooking, and I’ve been doing a lot of that lately.”
“Really?” Robin asked excitedly. “Which book?”
Chad told her.
“Is it really that good?”
He glanced down at his body in answer. “I guess it’s working better than I thought it would.”
“How bad are the recipes… I mean how do they taste?”
Chad smiled. “Most of them are really good. But a few…” he shook his head.
“Isn’t that the way it always is? Well, I got to tell you, they’re sure working for you. Everyone was pretty impressed with how you’re looking. You ‘really’ should have been there this afternoon.”
Chad smiled once again. For once he had had a better excuse to avoid the humiliation. “No thanks. Besides, I did get a lot done while you were gone.”
“Glad to hear it,” Robin replied with a smile. Then she rolled her eyes, “All that clicking from those stupid long fingernails of yours on the keys was about to drive me crazy!”

It wasn’t till very late in the afternoon that Mel had a chance to check her email and read the paper that Chad had sent her. She didn’t really care much about the contents, she had been more interested in keeping Chad away from Robin. But did it? She could only hope so. It seemed like he had finished it fairly quickly, and overall, it was mildly disappointing, telling her that he really didn’t know much about fashion – even after doing the paper. But that hadn’t been her main goal anyway.
She had told him that she would spend some time with him tonight, sorting out some outfits that he could wear to work. She’d discuss it more with him then. But sorting out outfits wasn’t the only thing she had planned for tonight. She sat back in her chair and closed her eyes… and smiled. Yes, she was definitely looking forward to later. Opening her eyes again, she quickly began typing an email to him, relaying her instructions for the evening.

Chad drove home with only one main thing on his mind – getting out of his wet and messy diapers and getting cleaned up! He had been peeing more than usual all day. He realized now that that was because of the waist cincher and all the extra pressure it was keeping on his bladder. At least the total amount that he had peed didn’t seem to be any worse than usual. Not as far as he could tell anyway. He was just doing it more often.
Mel’s instructions for the evening were exactly what he had expected – get cleaned up and into his uniform and get dinner started. For once, he was looking forward to a normal evening, one where he wouldn’t be subjected to humiliation after humiliation – he hoped.

Mel unlocked her apartment door and opened it to the smell of something delicious cooking. Even before she stepped inside, she closed her eyes and breathed the delicious smell in fully. “Mmmm.” Continuing in, she dropped her purse and laptop bag on the table by the door and walked into the kitchen. Sissy was there, in uniform of course, working on dinner. His back was to her as he was working at the stove. “Smells good,” she said as a way of announcing herself.
Chad turned his body as he was in the process of tasting some sauce from the wooden spoon in his hand. He quickly dropped the spoon back into the pot and turned around. Dropping a curtsey as he was supposed to, he said, “Welcome home, Mistress.”
Mel smiled with delight. Oh how she loved this! “How’s dinner coming?” she asked.
“Almost done. Just a few more minutes.”
“No hurry,” she replied with a small wave of her hand as she turned and walked out. “Just let me know when it’s ready.” As she walked off, she thought again about Chad. Yes, he was really getting to be perfect. A man… a man that she was forcing to act more and more totally like a woman… all the time… and not just a woman, but her maid… and… the darn guy was a great cook! Yes, perfect! And the thought of it sent a small wave of sexual excitement though her… which immediately set her to thinking about – later.

Mel savored the flavor of the food in her mouth – delicious! Her eyes were focused mostly on Sissy who was standing as usual in his corner, on his bar. He hadn’t moved hardly at all the whole time she had been eating. He was really getting much better at it. She wondered briefly what he must think about as he stood there with nothing else to do and no other stimulation at all. Not her problem. But it was certainly her delight to see it.
With her meal finally done, she picked up her drink and wandered into the living room. Instead of releasing him, she selected a chair where she could sit and watch him better. She had no doubt he knew she was no longer at the table. But she was pleased to see him not moving anyway. Did the bar he was standing on hurt as much as she thought it did? He was certainly tolerating it well enough. She thought again about his fantasy of being trained so that he could wear nothing but high heels all the time. Should she do it? His perch was certainly good training for that. Just keeping him in heels all the time would probably do it. But heels weren’t practical shoes for a maid and the work a maid needed to do. But was his work that difficult anyway? Would it matter? She really wasn’t sure. It was something she’d have to think about a bit more.

Chad stood on his perch with his eyes closed, trying extra hard to not move at all. He had heard Mel come out and sit down near him… he guessed anyway. Why wasn’t she releasing him? There was work to be done. Dishes to clean. Not to mention the fact that he was getting really hungry. Just eating baby food for breakfast, then a really light lunch had left him fairly hungry. And he hadn’t eaten a lot of solid dinners lately. Baby food just wasn’t very satisfying. Come on, Mel. Release me! His toes were aching from standing on the bar. His calf muscles were aching from standing on the bar. He wanted to move his feet and legs so badly, but the damn bar prevented that. His whole body wanted to move, but he dared not, especially with Mel so close by. Come on, Mel! Release me!
He suddenly felt the need to pee again. Timing himself wasn’t really an option just then since he couldn’t glance at his watch, so he let it out. Pleasure, pure pleasure. Not to mention a brief distraction from his corner predicament. Unfortunately, it was too brief a distraction.
“Ok, Sissy. Get your dinner.”
The words were like a gunshot, breaking the silence in the room and actually startling him a bit. But they were very welcome words. He painfully extricated himself from his corner perch and flexed his ankle and leg muscles a bit before heading back into the kitchen. He pulled his dinner out of the refrigerator and carried it over to the table and set it down. He might have had to keep it in the refrigerator while Mel was eating so it would no longer be hot, but even cold, it would be a very welcome change from all the baby food he had eaten lately.
Very much aware of Mel’s scrutiny, and knowing she wouldn’t approve of him sitting at the table with it, he pulled the tray off of his highchair, climbed up into it, and pulled the tray back in place. But with the big tray in the way, locking him into the chair, he couldn’t reach his plate of food that he had left on the table. “Um… Mistress,” he called. “I seem to have a problem.”
Mel got up from her chair and headed toward the kitchen mildly amused. “Aw… Does the baby need some help?”
“Yes, please.” He felt so childish sitting in the highchair, unable to even put his own dinner on the tray in front of him.
Mel picked up his plate and set it on the highchair tray so he could start eating. But instead of going back into the living room, she chose another chair at her table to sit down where she could watch him. His hands and face were quickly becoming a mess since he had to eat everything with only his fingers. He quickly looked more juvenile than ever, despite the fact that he was wearing his maid’s dress instead of one of his more babyish outfits. She felt a slight tingling in her sexual regions from just watching him. Later, later, later… but not much later. She doubted she could hold out that long.
“So did you get to spend much time with Robin this afternoon,” she finally asked. That was the primary question on her mind. Did her assignment do the one thing she wanted it to?
He looked at her, his face and hands incredibly messy from his dinner. She had to stifle a giggle. “I couldn’t,” he replied. Between all the work I have to do on our project, and then that writing assignment you made me do, I didn’t have time to do anything else.”
His words made Mel very happy. It had worked! She’d have to come up with a few more assignment like that for the future.
Chad went back to eating his dinner, while Mel just sat and watched him. For as hungry as he was, he was very surprised to find himself very full before he even finished. He had to force himself to eat the last few bites that he ate, and still he left some of his meal unfinished. He looked up at Mel, slightly surprised at being unable to finish his meal. “I can’t eat anymore.”
Mel looked at him slightly surprised. “You don’t like it?”
“No, I love it. It’s really good. I’m just so full suddenly.”
Mel just shrugged and got up from her seat. Instead of pulling his tray away from him right away, she got a washcloth and washed his hands and face with it… like the baby that he was gradually becoming more and more of. She picked up his plate and set it on the table, then pulled the tray away so he could get down. He quickly dropped another curtsey and said, “Thank you, Mistress.”
She smiled with delight as she handed him the tray. “You’re welcome, Sissy. Clean up the kitchen now.” She wandered back into her living room to watch some TV for a while, while her maid did “her” work.
Chad grabbed a baby bottle of Mel’s tea to help wash down his dinner while he worked. He was still surprised that he hadn’t been able to finish his dinner. He had been really hungry before he started, but he just hadn’t been able to eat as much as he usually did. Too many really small meals lately, he decided as he put a pan into the sink to wash it. And then the urge to pee suddenly hit him again and it made him think about his waist cincher that had been causing him to pee more often all day. That was another reason he probably couldn’t finish his dinner. Maybe the main reason. His darn waist cincher was compressing his stomach too much. If he had to wear one too often, he figured he’d be losing even more weight. Sigh!

Friday, July 16, 2010

The Bet - Chapter 26 (Wednesday – week 4 Part 3 of 6)

The Bet
by Karen Singer

Chapter 26 (Wednesday – week 4 Part 3 of 6)

Mel closed the cover of the folder she had been working in and set it aside on her desk. She picked up the next folder to work on and paused. She was working hard. Was Chad? What was he doing today? He had said that he still didn’t have the go-ahead to get back to his project. Was he and the Robin woman spending all their time together again? The thought of it disturbed her. To take her mind off of it, she opened the folder in front of her and plunged back into her own work.
But it didn’t last. All she could see in her mind was Sissy and Robin talking together. Sissy, sitting and staring into the eyes of the beautiful, young Robin woman. She couldn’t stand it! She closed the folder in front of her again and stared at, hardly seeing it. How could she keep him from spending all his time with Robin while he was at work? The problem was that he was supposed to be working with Robin. But they weren’t working. Not just then anyway.
Maybe that was the solution. She couldn’t do anything about giving Robin any work that would keep her away from Sissy, but maybe she could give Sissy some work that would keep him away from Robin! But what?

The hallways were crowded as Chad and Robin walked back to their desks from the break room. Chad still did his best to not look at any of the men, he was too embarrassed about himself for that. He was embarrassed about being seen by the women too, but somehow they didn’t seem so bad to him just then.
As he sat down in his chair again, he noticed that the irritation from his diaper rash didn’t feel quite as bad as it did earlier. Was it finally clearing up? He could only hope.
He glanced at his computer and noticed an email had come in. He opened it. “Oh Roooobiiiin,” he called over the cubicle wall. “Check your email!”
A minute later, he heard Robin’s voice exclaim over top of the wall, “Finally!”
Chad walked around to her cubicle where she was just reading the email. “It took them long enough,” he declared as he walked in.
But Robin was intent on reading the details of the email and didn’t answer right away. “Did you read all of this though?”
“Not yet,” he answered.
“They not only liked what we did, but now they’re asking for a lot more… a lot!”
“Ok,” Chad replied as he leaned over her shoulder to read her screen. “I guess we’re suddenly busy again.”
“I would say so,” Robin replied.

Mel paused while typing the email message and glanced at her watch, it was lunchtime… a little past actually. Darn! Chad wouldn’t even be at his desk now. But that really wasn’t a problem. He’d get his instructions as soon as he got back. She finished typing her email to him and hit the send button. There! That should do it!
With a smile, she closed her computer and got up from her desk, wondering if Andrea would like to go to lunch with her for a change.

Chad pulled into the parking lot at the gym feeling happier than he had all day. He wasn’t happy because of what he was wearing. He was happy because he was definitely sure his diaper rash wasn’t as bad now. It was still there, just not so bad. Even all the wetting he had done that morning hadn’t made things worse. Now if he could just convince Cassie to not give him one of those suppositories…
He walked through the door into the gym and was immediately greeted by the receptionist who called out, “Hello Sissy,” all too loudly – and with a far bigger grin on her face than he was happy about. He immediately dropped a quick curtsey and said “Hi.” Then he waited till she found Cassie for him. He again repeated his curtsey and greeting for Cassie, then followed her back to their usual private office.
“How’s your rash today?” she asked, as he began undressing and she was closing the blinds.
“I think it’s starting to get better now,” he replied.
“Well, that’s good,” she said. “It looked pretty bad yesterday.
Chad waited till he had struggled to get his pantyhose off, then his girdle before he asked. “Look, is there any way we can please skip the suppository today? The rash is getting better, but the mess from the suppository will only make it worse again.”
She looked at him and smiled. He had the distinct impression that she just might go along with him for once. “Nope! Sorry. Mel’s instructions.” His hopes were dashed once again!
Cassie spent very little time working on the front of him – there just didn’t seem to be any point in it anymore. Since the chastity device prevented her from touching his penis directly, he wasn’t going to get any kind of a reaction as she worked on him there. He got very little of his bottle finished by the time she had him roll over onto his back and pull his knees up under him – exposing himself shamefully for her attentions. Attentions that he was now rather looking forward to – as long as she didn’t mess with his diaper rash too much.
As she carefully spread the ointment sensually over his red and blistered bottom, her hands still felt wonderful. Yes, the diaper rash was definitely better today – since he was getting that much pleasure from her rubbing her hands over it.
Even still, she didn’t spend long on it before he again felt the cold, hard tip of her toy playing with his asshole once again. He braced himself for it, and felt her pushing it into him, slowly… ever so slowly today. She was teasing him with it. He wanted to push himself forcefully onto it… impale himself fully. But this time, he restrained himself. He didn’t push back at all. He simply waited and let her push it slowly into him, then pull it back again, then push it a bit further… teasing him with it. She was doing all the work today, not him. He closed his eyes and gave himself to the sensations he was feeling. Why did he have to love this so much? It wasn’t right! It was wrong! Wrong! Wrong! He mentally sighed. It did no good to berate himself. He loved it, and that was all there was to it. He just did.
But as Cassie played with him, the stimulating feelings grew inside of him. They finally reached a point where he could no longer be just the passenger. He had to have more! He finally pushed back, then pulled away, then pushed again… faster and faster… harder and harder… searching, desperately trying to find enough feeling and sensation to get over the hump – the hump that would grant him sexual release. But it just wasn’t to be. No matter how hard he fucked himself against her toy, he just couldn’t get there. He finally stopped, totally frustrated.
He felt her pulling the toy out of him, then inserting her finger in him once again, pushing the suppository way up inside of him as far as her finger would go. He prayed that for once it wouldn’t do anything so his rash could continue to get better. But he knew all too well what would probably happen. As she pulled her finger out again, he opened his eyes. In his present position, he could just barely see his chastity device. His penis inside of it was no bigger than it ever was anymore. Not one bit bigger. Since Mel had put the new teeth into the device, his penis stayed smaller and more insignificant than ever – always. It had to, or the pain would be awful.
As he rolled over so Cassie could continue diapering him again, he tried to remember the last time he had felt any pain from those teeth – last night when Mel had dressed him in that ridiculous baby dress. The pain had been horrendous. He had no choice but to try to ignore his feelings of sexual stimulation so he could always remain small. Not just small, but tiny. And now, because he couldn’t ever get hard, and because he was loving the sensations from his asshole so much, he was starting to associate that area of his body with pleasure instead of his penis. It was like another small blow against him to realize that his penis was now becoming totally useless to him for anything except to pee out of. No pleasure from it at all. No reaction from it could be allowed at all… no matter what stimulation they threw at him. More and more of his pleasure was coming from his asshole instead. Mel was slowly stripping yet another male trait away from him. And once again, the very thought of it thrilled him sexually inside… there was just no reaction from the very place where there should have been one… his penis.
He picked his baby bottle back up again and sucked on it while Cassie finished with him. He barely registered what she was doing, his thoughts instead were locked on his more than ever useless appendage. Less of a male. More and more… less of a male. Mel seemed to be slowly winning the battle, at least in some areas. But how about the one big area that the bet was centered around – total incontinence? The thought of it made him realize that he had to pee again. He held it – purposely. Even though most of him wanted to just give in completely… she had stripped everything else away from him anyway, why not just give up? Part of him wanted to. But another part of him made him still hold on. That part was still fighting back.
He was slow to finish his bottle, lost in his thoughts, laying there on the floor in only his diaper. Self-respect, friends, and a life… not to mention relief… if he could still get any. He remembered how he had been last night, sitting in Sandy’s living room, crying and sucking his thumb. He had lost so much. He had no choice but to fight back! He sucked harder on his bottle to finish it faster so he could get out of there now. Cassie was sitting there staring at him, waiting on him. He finally began dressing again while he continued to finish his bottle. He had to fight back! Self-respect, friends, and a life!

Chad sat in his seat again, gingerly, but easier than he had before, since his diaper rash had improved a bit. Robin wasn’t back yet so he opened up the spreadsheet that he used to track his progress for the bet. Next to yesterday’s date, he filled in twenty-six minutes. Only one minute longer than he had managed the day before. It was progress, but certainly not much. He promised himself he would try a lot harder today. He checked the number of days still to go – thirty seven. Still more than a month. An eternity in some ways. Yet it gave him more time to build up his strength holding back. The only thing that really worried him was all the progress that Mel had made against him already in other areas. Surprising progress. Would he be able to keep his control – the control that would let him win the bet? He knew himself well. His body always regained everything quickly. But would he be able to make it? As far as the bet went, he was sure he could do it. His bigger question now was the other areas, especially his more and more useless penis when it came to sex. Would he ever get full use of it back too? That was a more troubling question.
He noticed an email waiting for him so he opened it. He was surprised to see that it was from Mel. What did she want now?


Since you seem to have so much free time on your hands, I want you to put it to good use. You said you’re having trouble deciding on outfits to wear. I want you to write me a fifteen hundred word paper – all about fashion and mixing clothes for different occasions. I expect you to email it to me before you leave work this afternoon. You can research everything on the internet. Do it, and don’t disappoint me!

Chad couldn’t believe it – a fifteen hundred word paper? Something like that would probably take him all afternoon, and then some. He reread the email again, then went back to the first sentence. He realized that Mel thought the approval for his project hadn’t come through yet. With a smile he opened a return message to Mel and explained that he and Robin now had the approval on their project and he was going to be too busy to do the paper for her. He happily pushed the button to send the message back to Mel. Then he put her whole paper out of his mind. One less thing to worry about!
Half an hour later, he was busy working on part of the project, when he saw another email come in. He paused in his work to open it and was not surprised to see that it was from Mel. He was surprised however at the contents.


I don’t care if you think you’re busy. I gave you an assignment and you better carry it out – no matter what! If not, then your diaper rash will be giving you far greater torments – for a very long time!

Chad stared at the email, totally aghast. Far greater torments? He had no doubt that she’d whip him severely for not doing her assignment. He closed the email and deleted it. A fifteen hundred word paper. And he had no choice. He would have to do it… probably before he did anything else for his job… or more likely, he’d have to do it while he was doing his job – both things at the same time. He only hoped that Robin wouldn’t notice what he would be doing.
He held up his hands and stared at the long claws that were his fingernails. He was going to have to type an awful lot with those claws? It would take forever! His nails gave him even more reason to hate doing Mel’s “assignment.” With a dejected sigh, he opened up his web browser to start doing research.
Only a few minutes later, his afternoon suppositories kicked in. As usual, he didn’t bother to fight against the inevitable. What would be the use? He’d only be making himself more miserable. As the mess gradually slid out of him and around his diaper covered backside, his primary thoughts were not so much the paper he was writing for Mel, or even the work he was supposed to be doing for his job, he was mostly thinking about his diaper rash and how much worse it was about to get.

Tuesday, July 13, 2010

The Bet - Chapter 26 (Wednesday – week 4 Part 2 of 6)

The Bet
by Karen Singer

Chapter 26 (Wednesday – week 4 Part 2 of 6)

“Hi Chad,” Robin’s voice called breathlessly as she hurried past his cubicle. She was running a bit late… not that anyone would really care. But before she got fully into her own cubicle, she stopped short. Had she noticed his bare legs again as she walked past? She had the distinct impression that she did. Of course, she had been hurrying and had just barely glanced. With her arms still heavily loaded, she took a few steps backwards till she could just see into his cubicle again, and this time she quietly took a closer look. “Sissy! You’re all dressed up again. And that’s the same outfit you wore last week.”
Chad turned around at the sound of her voice. He was startled because he hadn’t heard her come back. “Hi Robin,” he replied as he felt himself blushing. He looked briefly down at himself. “Is there something wrong with this outfit?” he asked, still unsure of himself.
She stared at him, totally surprised at his question. “You’re a guy, who wear’s nothing but women’s clothes every day, and you’re asking if there’s something wrong?” She shook her head. “For what you are, it’s great!” She shook her head one more time and walked back to her own cubicle so she could unload all the things she had been carrying.
Chad stared after her. For what he was? What did she mean by that? He got up and followed her around to her own cubicle. She had set a large pile of things down on her desk and was just opening her big bag as he got there. “What do you mean, for what I am?” he asked.
She pulled her big mirror out of her bag to check her face, but before she could look into it, she stared at him instead, totally annoyed by his question. “What do I mean? Well look at you, for God’s sake! Obviously, you’re one of those stupid transvestite people. Only one who seems to carry things further than most that I’ve read about.” She looked at him more carefully. “Or are you really… what do they call themselves… transgendered or something? One of those men who are actually trying to change what sex they are. Because that’s what you seem to be!”
Now it was Chad’s turn to be surprised. “Me? Transgendered? Is that what you think?”
“Well what else am I supposed to think?” she asked testily. “It’s not exactly normal for a guy to suddenly turn up in women’s clothes and then that’s all he wears from then on.”
Chad shook his head. He supposed what she thought only made sense. No doubt it was probably the impression he gave everyone. But because of the bet, he had no choice in the matter. “That’s not exactly it,” he said softly.
“So what is it?” she asked, still agitated.
He shook his head again. “It’s complicated. I don’t want to talk about it.”
She almost threw the mirror in her hand at him. “Get out of here!”
Chad quickly retreated back to his own cubicle. What was eating her today? Ok, maybe she had a right to be angry at him, but he still couldn’t explain anything to her. The last thing he wanted anyone else to know was about the diapers he had on under everything else… or even about the bet itself! He supposed he’d just have to keep giving everybody the impression that Robin already had. He smiled to himself. It was somewhat true. He did like wearing women’s clothes… deep down. It was totally humiliating… but he did like it.
He turned and faced his computer. The email this morning had still not contained anything about the project they had been working on. So what was he supposed to do with himself again all day? He leaned back and laced his hands behind his head… and noticed his skirt, and his pantyhose covered legs. Damn! He was actually doing it again! He was actually wearing a skirt – at work! He still found it hard to believe.
He stood up and looked down at his clothes. If he leaned over far enough, he could see past his breasts and the hem of his skirt all the way down to the tips of his shoes. He swung his hips back and forth a few times to watch the skirt swish around him. It was fascinating to see how it moved… not to mention how odd it felt against his legs.
“What are you doing?”
Chad jumped at seeing Robin leaning around the edge of his cubicle. He immediately felt his face blushing a deep red. What could he tell her? “I’m just trying to get a feel for how this skirt moves,” he replied. Well, it was the truth… mostly.
She nodded. “Yeah, I can see that.” She came all the way into his cubicle. “By the way. I’m sorry if I sounded angry earlier, the baby had kind of a rough night last night.”
Chad nodded. “Didn’t get much sleep?”
“Not really.”
“Diaper rash bothering him?” Chad asked… hopefully.
Robin looked at him strangely. “Diaper rash! Not on your life. That’s easy to fix. No, sometimes he still gets colicky and he can’t sleep. He cries for hours.”
“Oh,” Chad replied. “Sorry to hear that.” He really wanted to ask her about how she fixed her baby’s diaper rash, but he chickened out. Instead, he looked back down at his skirt, then back up at her. “So is there really anything wrong with wearing this again?”
She shook her head. “Of course not. It’s just the same thing you wore last week – the last and only other time you wore a skirt to work. I just would have figured you’d wear something different this time. That’s all.”
“Oh,” he replied as he pulled on his top, stretching it back down into place again after the swishing back and forth he had just done. “The truth is, I didn’t know what else to wear today.”
“And you didn’t want to wear slacks like you usually do?”
“Um,” how could he put it without giving anything else away… “not today.”
“Well, just to be different, you might try getting a few more skirts and dresses… if you’re going to be wearing them, that is.”
He shrugged his shoulders. “Actually, I’ve got quite a few.”
“So why did you wear the same thing again?”
He shrugged his shoulders. “I’ve got several skirts and a bunch of tops, but I don’t know how to mix and match them together.” He looked down at what he was wearing again. “I know these go together so there’s no problem.”
Robin looked at him trying to figure out if he was serious or not. He certainly seemed serious. When you bought your other clothes, didn’t you buy things that you had some idea what you’d be wearing with them?”
Chad shook his head. “Not really.” He couldn’t tell her that it was Mel who had picked out most of the things he had now… except for the few things he had had from before.
Robin shook her head. “You might want to think about that the next time you’re out shopping.”
“Yeah, I’ll do that,” he agreed sheepishly. It was a thought, knowing in advance what would go with what. Even when Mel was picking them out.
He sat down again in his chair. But instead of leaving, Robin moved all the way into his cubicle and leaned against his desk. “So what other clothes do you have… women’s clothes that is?”
Chad raised his eyebrows at her question. The last thing he expected to be discussing with her was the contents of his closet. “Well,” he began, trying to find a place to start.
“Do you have a lot?” she asked, interrupting him before he could get started.
He shrugged. In the last month, Mel had made him buy a lot more than he had ever planned on. “I guess,” he replied.
“Wait a minute then,” Robin said just before she hurried out. She came back a moment later, pushing her chair ahead of her. “I may as well sit down while we talk. This should be interesting.”
Chad was a bit surprised by her forwardness, but he shrugged it off and began describing the contents of his closet – purposely leaving out his maid’s dresses and anything else he didn’t want her to know about. With every item he tried to describe, Robin grilled him for more information as to style and color and in some cases, who the designer was. But she quickly learned that Chad knew nothing at all about the clothes he had. He couldn’t even describe the colors or the prints properly. “Geez, for a sissy, you really don’t know anything,” she declared at one point, thoroughly disgusted and frustrated with his lack of knowledge.
“For a sissy?”
“Well, yeah. Don’t most guys like you know a lot about this stuff? I thought they did anyway.”
“Obviously not,” Chad replied. Despite her comment, and despite the awkward topic for him, he suddenly felt like a bit more of a failure.
“I mean… geez! A four-year-old girl knows more about her clothes than you do. It’s like talking to a complete baby!”
Chad was completely taken by surprise by her statement. Especially the part where she practically called him a baby. Worse, he knew she was exactly right… more right than she even realized. “Uh,” he said, trying to find some way to reply.
“Look,” Robin said. “I’ve got an idea. We’ve got nothing better to do anyway.” She disappeared for a few moments, then came back again with a handful of magazines. She set them on his desk in front of them. “Let’s go through these together. I’ll point to some pictures, and then you tell me if you have anything even remotely similar. Ok?”
Her idea startled Chad a bit. It also embarrassed him some. But he agreed to go along with her suggestion – mostly because he was truly interested… deep down inside somewhere. Besides, he had a feeling she wasn’t exactly giving him a choice in the matter.
Robin flipped through the pages of the magazines, stopping often to point at pictures and comment about the clothes the model was wearing. Despite having nothing to really say about the pictures she was pointing at, Chad found this far more interesting than just looking at the magazines on his own. Then, something about a skirt in one of the pictures caught his eye. “Wait a minute,” Chad said, leaning forward to peer at the picture more intently. He pointed to the skirt the model was wearing. “I’ve got one that’s almost just like that. But mine doesn’t have a belt like that one.”
Robin peered closer at the skirt he had pointed to… happy that he had actually been looking for clothes that were similar to what he owned. “Yeah,” she said with a lot of interest. “That’s a nice one. Nice color too. It looks like a basic A-line skirt. You could probably wear that with almost anything.”
Chad felt glad that he had finally found a picture that was similar to something that he had. As Robin kept turning the pages, he had to stretch his imagination a bit to relate the clothes that he owned to anything in the pictures. But the process was really made a lot more difficult because he didn’t remember much about most of his newer clothes since the only time he had ever worn them was in the dressing room at the store. Yet he tried his best to find matches for Robin to see.
It was a while later, that he realized how interested and comfortable discussing the clothes and the fashions he had become with Robin. Surprisingly comfortable. And dare he say it, he was really enjoying himself. Was he finally getting to the point where he could enjoy talking about feminine things… or possibly just engaging in normal “girl-talk” without being embarrassed by it? He seriously doubted it. In fact, he knew he wasn’t. It was only the situation right there with Robin that made it seem comfortable for him.
Robin closed the magazine they were looking at and leaned back. “I need some coffee!” she declared. “Let’s go get some.”
Chad checked his watch. It was just getting close to everyone’s break time. “No thanks. Everybody will be heading to break right now.”
Robin looked at him and rolled her eyes. “Oh come on! Everybody’s seen you in that dress before anyway.”
Chad shook his head. “No thanks.”
Robin stood up, then stopped. “You’re being stubborn and stupid again,” she declared. She reached out and grabbed his arm and pulled. “Come on! You’re going whether you like it or not!”
“Robin… No!” he replied, resisting her efforts to pull him out of his chair.
“Look, if you don’t go willingly with me, then I’ll get everybody to come back here and drag you down there again!”
“You wouldn’t!”
“I did it before, didn’t I?”
Chad looked up at her in horror. “You would, wouldn’t you!”
“You better believe it!”
He shook his head. There was no winning with women… anytime. “I’d rather not,” he said… trying to get out of it one more time.
“Get up and walk!” she ordered as she pulled again on his arm.
“Ugh!” he grunted in total frustration as he got out of his chair. He was heading for yet more humiliation that he didn’t really need just then – or anytime for that matter. As he walked beside Robin toward the break room, he was more aware than ever of his exposed legs and the looseness of his skirt as it lightly brushed his legs. Just the fact that he was again wearing a skirt at work embarrassed him and made him feel extremely self-conscious. Despite the fact that his skirt was actually comfortable to wear, he felt very uncomfortable in it. He wasn’t used to showing his legs in public like that – especially at work… around all too many people that he knew. He felt silly and embarrassed doing it. He realized that even though the pants he wore now were all women’s pants, they brought him a lot of comfort just in the fact that his legs weren’t so exposed.
He was overly conscious of his skirt and his legs all the way to the break room. But halfway there, he was also aware that the humiliation from what he was wearing was again fueling his unrelieved sexual needs. Damn! And the closer he got to the break room and the people he imagined that would be there, the worse it got. He hated it! Yet he loved it! And his nervousness grew along with his sexual excitement as the break-room came into sight.
Nervously, he entered right alongside Robin, as if she could somehow protect him from some of the humiliation he knew he was in for. There were a few people already in the break room, pouring coffee or sitting together at the tables. Chad followed Robin to the coffee pot, then to Robin’s delight, further down where they each grabbed one of the donuts that were still left. Chad did his best to not look around the room while he got his refreshments… he didn’t want to see who might be staring at him. But as soon as he had a donut in his hand, he had no choice but to turn and look around the room for a place to sit. He wanted badly to go back to his desk, but instead he meekly followed Robin over to one of the tables.
As he and Robin started in on their donuts, they were joined by more and more women, who all seemed to make a point of saying “Hi Sissy,” a lot louder than he liked. Of course, he knew they were all just trying to be friendly – friendly that is, if being a friend meant humiliating him.
As they talked, Chad noticed other people in the break room out of the corner of his eye. He glanced quickly at them, then just as quickly glanced away. They were his friends too… or they used to be. They were the men who would no longer talk to him… not that he wanted them too. At least they all respected him enough to stay away from him – totally. He really couldn’t blame them. If he were in their shoes, he wouldn’t go anywhere near someone like him at all either.
He couldn’t help glancing quickly at some of the men in the room again. He inadvertently locked eyes with a man over by the coffee pot – a friend he had known fairly well… before. He saw his former friend scowl at him and purposely turn away, walking purposely out of the room. Chad couldn’t blame him a bit. Seeing his reaction only made him feel that much worse about his situation than he already did. But unfortunately, there was nothing he could do about it.
The conversation around him brought him back to where he was. It took him a moment to realize that Robin was telling everybody about what they had been doing all morning. Oh great!
“Girl, you need some accessories!” one of the women declared. “It ain’t about what top you wear with what skirt… it’s all about what you dress it all up with!” As she said it, she pulled on her long necklace with one hand and held her other hand out, proudly showing off the rings covering each of her fingers. The women all laughed.
“I don’t have many… accessories – yet,” Chad replied.
The woman laughed. “You come shopping with me sometime, Honey. I’ll find you lots of interesting things you can wear.”
Chad rolled his eyes a bit. “I have no doubt!” Fortunately, everyone around him, including the woman laughed heartily.
“By the way,” the woman continued, “how come you don’t wear any earrings? I’m surprised by that, ‘cause even guys are wearing them these days.”
Chad was totally surprised by the question. “I guess because I don’t have any,” he replied.
“Why? You got something against them?”
“No, not at all. I just don’t have any… yet.”
The woman smiled and nodded her head. “Yet! You got to at least have the basics, girl. Now it’s none of my business, but I’d think that someone like you would at least own a pair of earrings.”
“Um… maybe soon,” Chad replied. Actually, he had mixed feeling about earrings. Yes the thought of them excited him greatly, but at the same time, earrings would be like another nail in his coffin. And he wasn’t sure he really needed that. But should he get some? It was certainly a question worth considering… or dreaming about, which would be safer.
As they talked, Chad still felt very awkward around the women, especially trying to talk about the things they were discussing – which was mostly clothes… and him! Girl-talk. It was so inviting. Yet he still couldn’t bring himself to get fully into it or even allow himself to enjoy it. He had to wonder yet again, at what point in a sissy’s life is it ok to just relax and let go… and truly let yourself enjoy something like girl-talk. At what point? He wanted to… he just wasn’t there yet.