The Bet - Chapter 49 (Friday – week 7 part 1 of 6)

The Bet
by Karen Singer

Chapter 49 (Friday – week 7 part 1 of 6)

He was wearing diapers of course, but nothing else – not unless you counted the plastic panties and the pacifier in his mouth. The diaper he was sitting in was messy too – it bothered him a bit, but there was nothing he could do about it. As he looked around him, the bars of the playpen he was trapped in seemed all too confining. All too high. There was no way out of it. He got to his knees and scooted over to the bars and grabbed hold with both hands. His chin just rested on the top rail of the bars. He was on his knees, yet for some reason, he couldn’t get to his feet so he couldn’t climb over the top. He couldn’t get out. Stuck, like a real baby in a playpen.
He released the bars and sat back in his messy diaper again. The floor of his playpen was littered with toys – baby toys. With nothing else to do, he rolled over toward the center where he could reach them better. A stuffed lamb caught his attention. He grabbed it. The material it was made from felt soft and fluffy. A moment later, he pulled his pacifier out of his mouth and inserted the back of the lamb instead – just to see what it tasted like… just to see what it felt like – in his mouth. But it was dry and uninteresting, so the lamb came back out again and his pacifier went back in.
He was aware that he was wetting himself again. But awareness was all it was, and he barely gave it another thought. He wet himself so frequently it didn’t matter. There was nothing he could do about it anyway if it did matter. Wetting his diapers was simply a fact of life. Messing them too, for that matter. He had no control of anything anymore – just like a baby. And here he was, just like a baby, in a playpen, with nothing but baby toys to occupy himself with. And he couldn’t get out.
The sound of someone at the door caught his attention. He saw Mel walking towards the door, opening it, letting in… a flood of people! They would all see him like this! They would all see what a complete baby he had become! And since he was trapped in this playpen, he couldn’t get away! He couldn’t hide – anywhere!
“Ooo. Look at the baby!”
He looked to see Sandy approaching with a big grin on her face. Robin was walking right next to her.
“Just what he deserves!” Robin said with a smirk.
“Doesn’t he?” Sandy replied.
And then Mel walked up with a baby bottle in her hands. “Come here, baby,” she said. He worked his way over to the bars and pulled himself to his knees, his hands clutching the bars, he chin resting on the top rail again. Mel pulled the pacifier out of his mouth and handed him the bottle. He let himself lay back on the floor of the playpen again as he put the bottle to his mouth to start drinking it. There was laughter from all the people on the other side of the bars, but there was nothing he could do about it. He was trapped – here where they could all see him. And there was no way out of the playpen.
He felt himself peeing yet again, but that’s all it was – a feeling. Nothing more. It didn’t matter. For all intents and purposes, he had become a complete baby again – in everything except size. He was big – adult size – but the only functions he was allowed were those of an infant. Nothing more. He had been totally reduced to this state. Completely. No more adult things – only baby things. He wasn’t allowed to walk. He wasn’t allowed to talk in anything except nonsense. He drooled continually. He now needed something to suck on all the time. He wet himself helplessly, and he messed himself helplessly too. The only things he was allowed to occupy himself with were all baby things, nothing more.
A baby. Reduced. No more say in any matter. No longer deserving of any respect. A thing of ridicule. Reduced.
Through the self-pity of his dream, he felt the familiar teeth inside of his chastity device digging in slightly again. But as usual, it was more of a background reminder. As sexually charged as he was, his tiny penis never dared get any bigger anymore – not as long as those teeth were there to make sure he never would. And they were always there!
In his dream, person after person laughed at him… told him he deserved just what he had gotten… that he would never be anything more than what he was now… a baby! And he had no way to fight back, no way to argue with anything other than nonsense baby sounds… and no arguments to counter what they were saying anyway. Nothing. He had been… reduced.
All he could do was to lay on his back and drink his bottle – proving that everything each one of them was saying was true. The only other expression his body was capable of making, was to pee again, further proving everything that they were saying.
No way out. Useless. Helpless. Reduced.
The sudden shocking blaring noise from his pink clock radio jerked him harshly out of his wonderful erotic dream… grating at his nerves, setting his teeth on edge. It was so shocking that he couldn’t move for several moments as his muscles were all locked. But as soon as he was able, he rolled off of his blow-up mattress, knocking over empty baby bottles in the process as he hurried to turn off the irritating noise.
Silence! He took a moment just to breathe and recover from the rude awakening. Tiny remnants of his dream, not much more than feelings, still lingered in his mind. But as odd as it seemed, those remnants represented a wonderful erotic experience for him.
He climbed to his feet, starting to take stock of himself as he did so. The three super thick cloth diapers that Mel had put on him last night were of course much thicker and heavier now. As usual, he had wet a lot during the night and as usual, he had messed in them too. He could feel how much they forced his legs apart. They had been hard to walk in last night so he knew without a doubt that it would be much more difficult now. His breast forms hung heavily inside of the bra he was wearing. And his pacifier was in his mouth again. He hadn’t bothered to put anything on over what he was wearing because it would only be something else he would have to wash eventually.
He stumbled his way wide-legged out to the kitchen to see if she had left him a note. She had! But when he read it, it was hardly worth the effort. The same as usual, with one minor note added at the bottom to make sure he had his pacifier again. No problem.
He grabbed his usual three baby bottles out of his refrigerator, noting as he did so that his supply was running low again. Well, it was Friday, so that was about normal. He put his pacifier down on the counter and carried his bottles out to the only piece of furniture that he owned – his one single solitary chair – that faced a wall of things he’d rather not look at. Closing his eyes, he put the first bottle to his mouth and began drinking. He immediately felt himself peeing again, but it was not anything he was going to do anything about. He was way too early to even think about holding back yet. And with all the bottles he would have to drink before he left for work, it would probably be late morning before he could even try.

Mel gave up trying to sleep and got out of bed. Her alarm would be going off in a little while anyway. She hadn’t slept well, and now that it was morning again, sleep seemed to be out of the question. She was too worried over what she was going to do about Sissy. She slipped her robe on as she headed out to make her morning coffee. But as much as she needed her coffee, her brain was already in gear and worrying about things.
Five minutes! How was she going to overcome that obstacle! It was the primary thing she had stressed over all night long. But along with that problem, she also remembered a few other things she had neglected to do last night. Easy things, but still things that needed to get done.
As soon as her coffee was making, she opened the drawer where she kept Sissy’s bibs. She pulled them out and started going through them. Finally she selected one that appeared to be perfectly clean – probably because it got used less than the others since it wasn’t one of her favorites. She folded it and set it aside for later. Then, since the drawer was open, she pulled out another one to use on him when he arrived for breakfast later.
She checked the coffee – as she expected, it was still making. She went to the living room and found her laptop and turned it on, then went back to the kitchen to wait till her coffee finished. Finally, with a fresh cup in her hands, she took a sip and headed back to her laptop where she opened up her email program. But what to say? Well, she would start with the obvious and go from there. Yesterday, Robin had sent her an email with a wonderful picture of Sissy in his diaper playing on the floor. Robin had sent a few tiny requests in the email. Now, she had a request for Robin. A big one!
When her email was finally sent, she relaxed a bit more than she had all night and took a bigger sip of her coffee. So good!

Chad stood in front of the long mirror hung on his closet door and checked his reflection one more time. Overall, he thought he looked pretty good – at least for a guy in a skirt. Make that – a sissy in a skirt. But skirts and dresses were the only clothes available for him now. Mel had removed anything remotely masculine from his apartment a long time ago. His hair was curled as femininely as he could for the length it was. He had applied his makeup as usual. The light blue crystal studs in his ears sparkled prettily. His cream colored blouse was fairly plain but the skirt he was wearing was colorful. His legs were encased in nude colored pantyhose and on his feet he was wearing tan strap-on heels. Of course underneath it all was his waist cincher, his all-in-one girdle, and of course his two diapers and plastic pants.
He looped the handle of his purse over one arm, and grabbed his diaper bag. In his other hand he grabbed the plastic bag containing all the empty baby bottles he had drank before he went to bed last night and again this morning. He paused just a second to brace himself for the day ahead. He had no doubt it would be another day full of humiliation. They always were. He opened his door and went out, heading for Mel’s apartment next door. He knocked and was rewarded by her opening it a moment later. He curtseyed. “Good morning, Mistress,” he said in his new sissy voice, lisping around the S’s.
“Good morning, Sissy,” Mel replied as she stood back out of the way. She started looking him over as he was walking in. As usual, her first impression was satisfactory. She waited while he stowed his things under her little table by the door, then she took a better look at him. Definitely acceptable. But he was without a doubt, a man under all the makeup and clothes. Again she wondered if there was any way she could feminize him even more… remove even more of his masculinity. But other than surgery, she had no clue what else she could do. But then, anything else would have to wait till after their bet was settled anyway, and there was only two weeks left to go. “Okay, Sissy. “Up in your highchair.”
A few minutes later, Chad was trapped in his highchair, a bib tied around his neck, eating baby cereal with a baby spoon held in his left fist.
While Chad was busy with his breakfast, Mel grabbed four more baby bottles from the dwindling supply in her refrigerator along with the bib she had gotten out earlier. She carried them to his diaper bag and put them in, removing the three bottles from the day before – two of which were still full. Those she could put back in her refrigerator for later. Even though he usually only used one of the three bottles she always sent, today she was adding one more. She closed his diaper bag up and went back to the kitchen to get a fresh cup of coffee and to watch him eating.

Chad got to the office before Robin. He knew because he checked her desk as soon as he got there. Yesterday she had suggested that he greet her with a curtsey out in the hallway every morning when she came in. But there was too much of a chance that someone might see him there. He wondered if he should actually do it. Yesterday she had been all over the place emotionally. There was a good chance she might not remember that today. Besides, what was the worst she could do to him if he didn’t? He stowed his purse in his desk drawer and booted up his computer.
Robin parked her car and got out. She was happy because she had left the house a few minutes earlier than usual so she could make a quick stop at the store before work. She had actually managed to get thorough the store fast enough that she wasn’t close to being late. She picked up the stack of magazines that she usually brought with her and grabbed her large bag that she carried every day and headed into the building. Would Sissy be out in the hallway to greet her like she has asked yesterday? She wasn’t at all certain that he would. A few minutes later, she turned down the hallway where her cubicle was located. There was nobody waiting in the hallway for her. It was empty… deserted. Was he here yet?
Her footsteps slowed and stopped as she reached his cubicle. She glanced inside. He was there checking his email. It looked like things weren’t going to bode well for him today!
Chad heard Robin stopping behind him. He turned quickly in his chair. “Hi Robin,” he said brightly in his old sissy voice.
But Robin’s reply wasn’t nearly as cheerful. “I know for a fact, that I asked you to be out in the hallway to greet me with a pretty curtsey every morning! I also know that I asked you to curtsey for me every time you spoke to me. Why is it, that you can’t remember those few simple little things?”
Embarrassed, Chad stood up and curtseyed. “Sowwy Wobbin,” he said contritely in his sissy voice.
“That’s not what I asked for,” Robin replied. “You were supposed to be in the hallway waiting for me to arrive. Now where are you supposed to be?”
With his head held down, Chad walked out to the hallway and stood near the entrance to her cubicle. He was about to curtsey when he saw someone walking across the hallway in the distance, so he just stood there for a moment and waited.
“What are you waiting for?” Robin asked.
Chad started to point to the woman who had been in the hallway a few seconds ago, but she was gone now. He curtseyed and repeated his greeting.”
Robin only nodded and entered her cubicle where she finally got to unload the armful of stuff she had carried in. She had to move the pregnancy t-shirt she had made him wear yesterday out of the way first. “This isn’t the way I had hoped to start my day!” Robin complained as she set her things down. “Obviously you thought I would forget what I told you to do.” She turned to face him, “Don’t deny it!”
Chad stayed where he was out in the hallway and looked nervously down at the floor.
Robin shook her head. “Once again you’re acting like a child and trying to get away with the least little thing!” She shook her head again. “I had planned for you to get some more work done this morning, but it looks like you may not get to it!” She paused for a moment before continuing. “I guess you need another time-out to help you remember!”
Chad’s eyes went wide! “No,” he replied quickly. “I’m sorry! I just didn’t… think.”
Robin pulled her chair away from her desk. “That’s right you didn’t think! Well I think… I think you better get down on the floor right now!” She pointed at the spot where her chair had just been – right in front of the corner of her desk.
Slowly and reluctantly, Chad went into her cubicle and got down on the floor preparing to go into the corner again. He started to push his way forward, but she stopped him.
“Where does your thumb belong?” she asked angrily.
Chad moved his thumb back to his mouth again, just like he had done before.
“Wait a minute,” Robin said, stopping him from moving again. She pulled her desk drawer open and again removed her roll of tape. A minute later, his thumb was again taped firmly into his mouth. “Okay, now you can get yourself in there. All the way in!”
Once again, Chad worked his way forward sitting cross-legged, till both his knees touched the walls of the corner. A moment later, what little light that reached under her desk got much dimmer as she sat down and pulled her chair into place.
“I think an hour under there should help you think about remembering things better!” Robin stated.
There was no way Chad could reply, not under her desk with his thumb completely blocking his mouth.

The Bet - Chapter 48 (Thursday – week 7 Part 7 of 7)

The Bet
by Karen Singer

Chapter 48 (Thursday – week 7 Part 7 of 7)

It was one of those evenings when Sandy could only meet with her client after work. It happened more often than she would like, but that was business. Her real problem tonight was that she was having a hard time concentrating on what her client wanted. Instead, her mind kept wandering back to the picture that Mel had sent. The note with it had been very short but it told volumes – “Robin has him drooling on her cubicle floor!”
Drooling! Why hadn’t she thought of that? But more importantly, a different thought kept running through her brain – she was the only one who seemed to really get off on seeing Sissy in his baby state. Was Robin another possible ally? Did Robin love it as much as she did? Everyone else wanted to humiliate a more grownup Sissy. She wanted to see him humiliated as a total baby. And now Robin had done pretty much the same thing with Sissy that she did.
As she listened to her client talking about drapes, her mind was instead thinking about the great t-shirt Robin had put Sissy in. Baby! With an arrow pointing down. Obviously a pregnancy t-shirt, but on Sissy the arrow now pointed at his diapers instead of a swollen belly. So perfect!
She had to talk to Mel! She had to contact Robin! She was sure that together they could come up with something great to do with him! Something really special!

Gloria was worried that Mel and Chad were going to be late again. But she saw them driving up at the last minute. She got up and met them at the door. As she did, she noticed that Chad was carrying his pink diaper bag with him this time.
“We need a minute,” Mel told Gloria as soon as they finished greeting each other. “I want to change him before we start.”
Gloria had no choice other than to let them do what they needed to. Actually, she didn’t really mind all that much at all. For the first time in a long while, she had no questions of her own that she wanted to ask Sissy. So the only thing on her agenda with them was a little normal relaxation and just a little hypnotism for Chad to get the answers Mel wanted.
Chad didn’t think he was leaking yet, but he knew he was close. So he was surprised when Mel had said she was going to change him. Glad too. He didn’t know how much he would be able to enjoy Gloria’s therapy if he was leaking.
Gloria waited patiently while Mel changed him right on the floor. She was a bit surprised that she made him drink from a baby bottle the whole time she was at it, but the two of them seemed to be comfortable and familiar with the routine. She wouldn’t have said anything about it anyway. Five minutes later, she was dimming the lights as both of them were getting comfortable on her couches.
She started with her usual routines, telling them how to relax. Telling them what to relax. But she didn’t move into the key words that would put Chad into a hypnotic trance.
Mel was listening carefully to Gloria, but she wasn’t relaxing. She wasn’t interested in relaxing. All she was interested in tonight was finding out how long Sissy was able to hold back. And this time, Gloria seemed to be going on and on and forgetting about Sissy. It almost seemed more like one of her old sessions, from before she had started bringing Sissy with her. Wasn’t Gloria going to hypnotize him tonight? The longer things went on, the more she started fidgeting and opening her eyes.
Gloria tried to coax Mel into relaxing, but she could see that Mel wasn’t cooperating at all. She finally saw Mel raise her head and start jerking it in Chad’s direction. She sighed a bit and rolled her eyes. Mel was too worked up with worry about Chad to enjoy the therapy. She gave up and started speaking the key phases that would quickly put Chad into a trance. Since she had done this with him a few times now, she knew she could get him very deep, very quickly.
To Chad, it seemed to take longer this time. Not that it wasn’t wonderful. It was. But it was the complete and total relaxation that he was finally now entering that he really loved. He felt good there. And safe. Totally safe. He didn’t just want to be in that place, he yearned for it. And that wonderful place finally accepted him eagerly and fully.
As Gloria leaned close to Chad to talk with him more directly, she saw Mel sit up on the side of her couch to pay better attention. “Remember,” Gloria told Chad, “the truth is very important. You want to tell me the truth.” She looked briefly at Mel before continuing with Chad. Mel was paying rapt attention. She turned back to Chad again, “Remember, you’re in the one place where you can feel totally honest with yourself. The one place where you must be totally honest. You are safe as long as you are honest.”
She glanced back at Mel again. Mel was mouthing something to her but in the dim light it was hard to decipher. “Front and back this time,” Mel whispered. Gloria nodded. She remembered.
She turned back to Chad. “Chad, you told me last time that you are still working on holding back. Are you still trying?”
Chad, his face peaceful, his eyes closed, nodded. “Yes.”
“Good, Chad. Tell me, are you trying to hold back your bowel movements too?”
Chad’s face looked more troubled. “Can’t.”
“You can’t hold back?”
Chad shook his head. “Can’t try. They keep sticking suppositories up inside of me. I can’t fight the suppositories. No point. Most of the time it’s coming out of me before I know it’s going to. Better to get it over with as soon as possible.”
Gloria looked back at Mel. Mel’s face looked happier now than it did a few moments before. She turned back to Chad. “Okay Chad, now how about your peeing? Are you still working on holding back there?”
Chad’s only answer was simple. “Yes.”
“And how are you doing?” She was surprised when the expression on his face changed, but it was an expression she couldn’t read.
“I think I’ve been having a pretty good week… considering.”
Gloria heard a small sound of surprise out of Mel.
“Considering what?”
“Considering that Mel is still making it impossible for me to even try to hold back whenever I’m not at work.”
“I see,” Gloria replied. “And how are you doing?” She suddenly felt Mel come up right behind her to look over her shoulder. Gloria did her best to ignore her.
Chad’s face clouded a bit. “Monday was bad. It usually is. The weekends seem to take way too much out of me. No chance at all to even try to hold back all weekend.”
“And why can’t you try to hold back on the weekends at all?”
Mel was frustrated with the question, she knew the answer to that one. She only wanted to find out how long he could hold back now!
“Too much to drink!” Chad replied. “Way too much to drink. After work too. And especially because of the time limit. Impossible to hold back at all with the time limit. I have to keep trying and trying to pee constantly. Even then I don’t always make it.”
“Okay Chad. That’s fine. So tell me, how long are you holding back now?”
Mel actually held her breath.
Chad shook his head. “Monday I could only hold it for five minutes. But I really improved Tuesday and made it to six! Wednesday I was down a bit to five and a half.”
“And how about today?”
Chad smiled as if pleased with himself. “Five minutes. The same as I started the week with. It’s not six, but it’s still pretty good!”
“So you can manage five minutes now?” Gloria repeated.
Chad nodded. “Yup!”
“Thank you Chad. Thank you for being honest and telling me. Now I want you to just relax again and think of nice peaceful thoughts. Thoughts that make you feel good. Thoughts that make you feel safe and relaxed.”
Gloria turned toward Mel. Her face looked troubled. “Is that it?” she asked quietly. “Anything more?”
Mel only shook her head and sat back down on her couch. Five minutes! And he had gained once during the week! Nothing about it sounded good to her at all! Nothing! What was she going to do? Last week it had been eight and a half minutes. Eighteen minutes the week before! She was trying harder and harder to make him incontinent – and making very little progress! What was she going to do? What could she do? For the first time, she really felt like she was losing the bet. There were only two weeks left! The objective seemed impossible.
She suddenly realized that Gloria was speaking the phrases she usually used to bring Chad out of his trance – the phrases that would end their session. She didn’t bother to lay back on her couch again. She was too wrapped up in her turmoil. What was she going to do? It was impossible!
Five minutes!

Chad sucked on his bottle, closed his eyes, and relaxed as Mel was driving them home. He felt so good! But once again, it was obvious that Mel hadn’t gotten as much out of the session as he had. He wasn’t sure why she bothered other than that she really seemed to need it – more now than before their session.
As soon as they got back to Mel’s apartment, he was ordered to take his skirt off so that his diapers would be on display again. As Chad was removing his clothes, he got the impression that Mel seemed to be very distracted tonight. What had changed her during their therapy with Gloria? She hadn’t seemed this way earlier.
Mel disappeared into her bedroom for a few minutes then came back out wearing only shorts and a t-shirt again. “Time for ballet practice,” she announced as she headed toward her stereo.
Once again, Chad had to work on the new routine that Mel had started teaching him the night before. And just like last night, their progress was hampered by her making him continuously stop to drink from his bottle. As far as he could tell, they were making good progress tonight since Mel wasn’t stopping him as often to tell him to do something better. They worked at it for several hours, and Chad was surprised when Mel suddenly told him that what he was working on was the final finish to the dance. They had managed to go all the way through it! The only break they had taken, other than for Chad to keep drinking, was to change him when he started leaking.
Chad had been afraid that the ballet routine that Mel was teaching him would be something totally humiliating, but the further they had gotten into it, the more he realized that this dance was something serious. It was intended to be feminine and graceful and beautiful, but he knew he wasn’t any of those things. Still, feminine and graceful were the two key things that Mel seemed to be trying to improve in his movements over and over again. As far as he could see, there was nothing at all silly about this dance, other than the fact that he was doing it. And the very things that would make him look most ridiculous, were the very things she was trying to train out of him. So he listened and did his very best to dance the way she wanted him to.
It was getting late and both of them were getting really tired by the time his diaper started leaking for the second time. That was the point where Mel finally called a halt to what they were doing. Chad felt proud over what he had accomplished, but he could see that while Mel had driven him unmercifully, she still seemed to be distracted by something else. She just wasn’t giving him a clue as to what that was. But other than driving him hard with dance practice, she didn’t seem to be punishing him in any way. So maybe it wasn’t him… he hoped!
As he hoped, when Mel changed him, she changed him into his night diapers, three of her super thick cloth diapers this time that left his legs splayed wide apart, making it difficult for him to walk. Unfortunately, as always, she didn’t forget to insert the stupid suppository again. A few minutes later, he was curtseying goodbye to her for the night – as usual, with her usual instructions to drink three more bottles before he went to bed. He was ready for bed, bottles or not. After so much dance practice, he was exhausted.
Mel said goodnight and watched him leave. But the door closing behind him seemed to haunt her… bother her… as if he was leaving her… abandoning her… for good. She suddenly felt lonely, as if she missed him – already. She couldn’t lose this bet! She couldn’t! Because losing the bet meant… losing him. Her mind pictured her fancy new house, melting into nothing. She pictured herself in her old age… alone, unloved, uncared for.
She shook herself, bringing her out of the strange thoughts that were running through her head. She wouldn’t lose! She couldn’t! But five minutes… and only two more weeks. It seemed insurmountable. She had again faked putting the suppository up inside of him. He wasn’t even trying to hold back from that now. Not as long as he still thought he was getting the silly little pills. That much at least was working. But it was the other… the part that still had five minutes of control that she worried about. How was she going to conquer it?
Five minutes. And he had walked out, closing the door behind him. “Goodnight, Sissy,” she said to the back of the closed door. “Goodnight.”

The Bet - Chapter 48 (Thursday – week 7 Part 6 of 7)

The Bet
by Karen Singer

Chapter 48 (Thursday – week 7 Part 6 of 7)

It was late in the day when Mel finally got to read Robin’s email. She laughed over the picture she sent. And this woman had asked for advice from her? Again, she was jealous that she couldn’t actually be there to see what she was doing with Sissy. She had to wonder again what Robin had wanted to talk with Gloria about. Maybe it had nothing to do with Sissy at all. She stared at the picture again and had a thought. A moment later, she had emailed the picture to Sandy. She knew Sandy would get a big kick out of it!
Robin’s little requests were nothing major, she could fill one of them tonight, but the other, well, probably, but she would have to see.

Chad was trying to hurry home as fast as he could. But it was one of those cases where the more he tried to hurry, the more the rest of the traffic seemed to slow him down. So he was getting nothing but frustrated in his attempts to hurry. Of course, the only reason he was hurrying was because Robin hadn’t even let him get up off of the floor until after she had left for the day. And then he still had to get dressed! He had even more of a reason to hurry tonight because tonight was relaxation therapy night – the one thing in his life that he really looked forward to every week.
He finally parked his car and hurried up the stairs to his apartment as fast as he could. He peeled all his clothes back off again and was finally able to deal with his messy diaper. But he had been doing that every day now for so long that he barely gave it more than a minimal amount of thought. A few minutes later, he was soaking his body in the shower to get himself clean at last. His shower didn’t last long though and he was soon phoning Mel to tell her he had just put his one diaper on again. He glanced at the clock. An hour and forty-five minutes till he had to be leaking. Why couldn’t Mel ease up when they were going out for the evening? It was such a major nuisance!
He hurried to get dressed again, for once glad that he would be only wearing one diaper and couldn’t wear the girdle or pantyhose that usually went over it when he went to work. He was glad only because the other items took time to put on and he was already running late. He had purposely tried to keep his hair dry in the shower so all it needed was a few brush strokes. Redoing his makeup took a bit longer though. He heard Mel entering his apartment and calling his name before he could finish.
“What are you doing?” Mel called as she closed the door to his apartment behind her. “We need to get going!” She found him in his bathroom still doing his makeup. “What’s taking you so long?”
Chad turned to her and curtseyed, and in his new sissy voice said, “Robin had me sitting on the floor in just my diapers. She wouldn’t let me get dressed again till after she left.”
Mel smiled momentarily. She had seen the picture that Robin had sent. “Just hurry up,” she replied as she walked out toward his kitchen. Most of the time, what Robin had done wouldn’t be a problem, not even tonight, but tomorrow night it would be a big problem because of their nail appointments. She’d have to remember to let Robin know about that later. She pulled a baby bottle out of his refrigerator for him and headed back towards his bathroom, hoping that he’d be nearly finished with his makeup.
Chad was just finishing his lipstick when Mel returned. He checked himself in the mirror. Hopefully it would have to be good enough for tonight. He turned towards Mel and curtseyed. “Good enough?”
Mel briefly looked him over. “Good enough,” she said impatiently. “Here,” she said she handed him the baby bottle. “Get started on it.”
A few minutes later, Sissy was sucking on the bottle in her car while Mel drove to their usual Thursday night restaurant that was located not far from Gloria’s office. As they pulled into the parking lot, all Chad could think about was the last time they were here – when he had wet his diaper so much that it had fallen off of him as they were leaving. He prayed things wouldn’t be as bad as that this week!
Unfortunately, when they got out of the car, Mel made Chad carry his baby bottle in with him since he wasn’t finished with it yet. The hostess recognized them immediately as they entered and this time didn’t even ask before she grabbed an adult menu for Mel along with a child’s coloring book for Sissy and a small box of crayons. “Right this way,” she said with a smile. In a way, Chad was actually glad that she had recognized them, he didn’t have to curtsey for her or use his stupid new sissy voice to talk to her.
The same waitress that had served them for the last few weeks was at their table as soon as they were seated. She immediately spotted the baby bottle that Chad had brought in with him. With a smile she asked Mel, “You want me to keep that thing full again?”
Mel nodded. “I’d appreciate it! Oh, and just coffee for me.”
The waitress checked his bottle and saw that it was still partially full. “Do you want that topped off now, or do you want to wait?”
Mel checked his bottle. “Bring me my coffee first. By that time she should be ready for a refill.” The waitress nodded and quickly left. Mel looked at Sissy. “I saw the picture that Robin took of you today.”
Chad blushed. He remembered her taking it with her cell phone. It was the circumstances he was in at the time that made it so embarrassing. He just hadn’t realized that Robin had sent it to Mel. He looked for some decent way to reply, but couldn’t think of anything. “I don’t know what got into Robin today,” he finally said. “She seemed to be in a lot of strange moods. One minute she was being nice and giving me something to work on, then later she didn’t want to talk to me, then later still it was like she totally exploded at me. And the next thing I knew, I was sitting on her floor like that, drooling around my pacifier, while I was playing with paper dolls. It was weird!
Mel nearly laughed. She could only imagine. Why had Robin ever bothered to ask her for advice? Maybe she should be asking for ideas from Robin instead! “Better keep drinking that bottle. I want it finished before my coffee gets here!”
Chad immediately picked up his bottle and put it to his mouth. As he did, he glanced around the restaurant, mostly out of the corners of his eyes. He saw a few people looking at him with shocked looks on their faces. He figured that by the time they left, there would be a lot more shocked people nearby.
When the waitress brought Mel’s coffee, she also carried a pitcher of iced tea as well. She set the coffee in front of Mel then took Sissy’s baby bottle and filled it. She was rewarded to see him put the crazy thing to his mouth and start drinking it immediately as soon as she handed it back to him. Something about it sent a small tingle into her sexual regions. Doing her best to ignore the feelings, she turned to Mel and asked for her order. As usual, Mel ordered for both of them – a kid’s meal for the strange one with the bottle.
“Don’t forget your coloring book,” Mel said as soon as the waitress had left, and don’t stop drinking either.”
Once again, Chad dumped the few crayons from the box out onto the table and started trying to color while the bottle was still in his mouth – obstructing his view of what he was doing. It wasn’t long before he felt like he was going cross-eyed again, especially since he had to hold the bottle up at an angle so he could keep drinking. And with only one hand to work with since his other one had to hold the bottle, the task was even more difficult. He seemed to be having to do all too many things lately with only one hand!
Mel watched him trying to color for a few minutes while he drank his bottle. He looked so ridiculous. She could see the other customers turning their heads occasionally to watch him. Some of them pointed. She was sure he was a major topic of conversation at most of the tables around. She briefly wondered how Sissy must feel about it – not that it mattered. Only what she wanted mattered. She was fairly sure that he was totally embarrassed about it, but as usual, he didn’t have a choice in the matter. The terms of the bet had seen to that – whether he liked it or not!
Before either of them knew it, the waitress was back again with her jug of iced-tea. She took the still half-filled bottle from Chad and filled it again, then handed it back to him.
“Don’t forget to say thank-you,” Mel prompted.
Chad wasn’t really grateful at all, but he dutifully complied. At least the words thank you in his sissy voice came out as semi-normal. He immediately put the bottle back to his mouth to continue drinking again.
“You’re welcome,” the waitress replied. But she didn’t leave. Instead she leaned over to look at the page Sissy was coloring. “Ohhh! Such a pretty picture,” she said. “And you’re coloring so nicely.”
Chad blushed. He knew he kept going out of the lines and red wasn’t the best color at all for someone’s skin. But he only had three crayons to choose from. It looked – childish!
The waitress turned to Mel. “You know, sometimes we take some of the pictures the kids color and hang them up on the wall over by the bar. If she does a really good job on it, I’m sure I can get it hung up with the others. You should put her name on it for her too though, that way it’s easier to tell who did what picture.”
Mel was delighted with the idea. She hadn’t seen the pictures since she never went near the bar in this restaurant. “Really? That would be great! I know Sissy will just love having her picture hung on the wall here. I’m sure she would feel honored! So many people could get to see it!”
“Before you leave, just give me the one you want to hang and I’ll take care of it.”
“Thanks, I will.” Mel replied brightly. As soon as the waitress left, she said to Sissy, “Wasn’t that nice of her? She must think you’re really doing a good job!”
Yeah right! Chad knew better. There was no way he could do anything remotely decent with only three crayons, one hand, and his baby bottle obstructing his view. Once again, his picture looked totally childish. And she wanted to hang it? She would!
Since Mel wasn’t letting him put the bottle down, Chad was forced to keep drinking almost continuously as he tried to color. The waitress came by and refilled his bottle twice more before their dinner arrived, and she refilled it again as soon as she had dropped their plates off. Even drinking continuously, Chad never had a chance to get the bottle much more than half way emptied. The only good thing about the situation… if you could call it that, was that by drinking only from his baby bottle, he was getting less fluid than when he drank from a glass.
Mel cut his meal up for him again into tiny pieces, then made him use only a spoon held as he usually did – in his left fist. As they ate, Chad asked Mel how her day was, figuring that hearing how her day went had to be better than talking about the embarrassing things he had to do. Once again, Mel told him what she could. How frustrating some clients were… and how dumb others seemed to be. She enjoyed telling him these things. It was nice to tell them to someone once in a while – someone who she knew wouldn’t be relaying her thought to anyone else.
As soon as they had finished eating, Mel looked at the pictures Sissy had finished. She selected one of them and carefully ripped it out of the book. She pushed it across the table to him. “Print your name on it. And make sure it’s big enough for anyone to read.”
Chad pushed his plate out of the way and grabbed a green crayon and started to put it to the paper.
“Wait a minute!” Mel stopped him. “You’re not drinking from your bottle.”
Chad picked up his bottle and once again started drinking before he signed the drawing. Now the task was that much more difficult. He barely made a mark with the crayon when Mel stopped him again. “Wait! Switch hands. Put the bottle in your right hand instead.”
Chad was a bit shaken by her demand. Switch hands? But the bottle soon went into his right hand and the crayon into his left. He started drinking again. His eyes started to cross the other way now as he had to look past the other side of the bottle. With the crayon in his left hand, it was difficult to just put it back at the end of the mark he had started making. But he managed it. He started to write the letter ‘S,’ but with his left hand, he started writing the letter backwards. He had actually gotten halfway though the top curve before he realized it. All he could do was to switch what he was doing in midstream and create the letter from where he had stopped. He heard Mel giggling across the table. He ‘S’ didn’t look very good at all, but he moved on. The ‘I’ wasn’t too bad, other than left handed it didn’t come out straight. But with only one hand he had to make the dot on top of it bigger than he meant to. Then he was faced with two more S’s. One handed, they came out crooked and childish looking too. Finally, he created the ‘y.’ Again, it was crooked and out of balance. The end result looked like a five-year old had signed it.
“Good job!” Mel praised as she took the drawing to look at it. I’m sure any kindergartener would be proud of it.
Chad felt so embarrassed! A minute later, the waitress dropped off the check, refilled Sissy’s bottle, and took the picture to hang on the wall. Chad wished she would just throw it away instead. When she came back, Mel paid for their dinner and left a very healthy tip. “Okay, Sissy. We better get going,” she said as she got up from her seat.
As Chad followed her out, he was aware that his diaper was very, very wet. But not nearly as bad as it had been last week. His only question now was, what would happen while they were in Gloria’s office. He had no doubts that he would be leaking very soon – which was good because his deadline was growing awfully near. And then he got a bit of a surprise, instead of going out the door, Mel went straight past it towards the bar area. The wall of pictures was easy to find, and so was Sissy’s picture. The waitress had started another column of pictures with his. So right at the top right side was Sissy’s picture – for all the world to see and appreciate.
“Oh,” Mel said delightedly. “I think that’s the perfect spot for it. Don’t you?”
Chad said nothing. He only noticed he was peeing heavily again in the midst of his humiliation.

The Bet - Chapter 48 (Thursday – week 7 Part 5 of 7)

The Bet
by Karen Singer

Chapter 48 (Thursday – week 7 Part 5 of 7)

Robin was actually getting things done when she happened to glance at her clock and notice the time. Break time! Finally! But she felt good about the work she had managed to accomplish. The only problem now, was Sissy. She was going to have to face him again and she still wasn’t sure how she felt about everything. She prayed he would just stay silent and not talk to her during break. Since she wasn’t really ready to deal with him yet, it would make things much easier.
As she got up from her seat, her eyes fell on the desk drawer where she had stowed her large bag earlier. Thoughts of what she had been thinking of doing with Sissy once again ran though her brain. But should she? Fortunately, it was break time. There were other things to do and think about. She went over to Chad’s cubicle and was glad to see that he was hard at work on the project and not goofing off doing something else. “Break time, Sissy,” she announced.
A minute later, the two of them were walking through the halls together. “Did you get a chance to look over anything I did yet?” he chanced asking excitedly.
For some reason, his question bothered Robin. “Some,” she replied, not wanting to really talk with him yet.
“Any problems with it?” he asked, hoping she could be a bit more forthcoming.
He just couldn’t leave things alone. He had to have approval for every little thing. Like a child trying to show off or win his mother’s praise. Since he bothered her, she said nothing in reply. Maybe he’d get the point and shut up! She was pleased when they actually made it to the break room without any more questions from him.
A few minutes later, they were both sitting at the women’s table listening to the gossip floating around the table. But Robin’s mind was more on Sissy. It had only taken a few minutes of being with him in the hallways to get her angry with him again. And once again he was showing her how much of a child he was. Why did he irk her so much? The discussion she had had with Gloria didn’t really help.
Once again her mind remembered the items she had in her bag for him. Was it cruel? Was she bad? She didn’t want to be cruel. She didn’t want to be bad. She wanted everyone to think nothing but good of her. She was a kind, loving woman. Not something out of a nightmare! No, she couldn’t do it! She wouldn’t do it! It wasn’t right! When they got back to their desks, she would apologize to him and do her best to deal with him in a normal – sane – manner. She suddenly felt a bit better about everything. She had made her decision!
As she took another sip of her coffee, she watched him sitting there, barely sipping at his coffee, listening to the other women talking, smiling and laughing occasionally at what was being said – as if he were another woman. But he wasn’t! She remembered him yesterday afternoon, right after break, when she had been talking to him… and he had suddenly messed in his diapers! The freak! She remembered making him strip down so she could see what he wore under his dress – and she had found his childish diapers and that… chastity thing underneath. The pervert!
He was pretending to be a woman! Pretending to be an adult! Pretending to be normal, like everyone else! But he wasn’t! Not even close!
She was aware of the anger building in her again just from looking at him. She didn’t like it, but she couldn’t help it. She was not a bad person! She was not cruel! She only needed to apologize to him. That was all!
The other women were suddenly getting to their feet to go back to their desks. Break time was over. Robin got up along with everyone else and followed them all out into the hallways – leading back to her desk. She would apologize to him. Just as soon as they were back at their desks and alone. She would do it! And it would be finally over. And she could no longer worry whether she was being bad or not.
“So you didn’t have any problems with what I did?” Chad asked again as soon as they were alone.
Why did he have to keep harping on it? Rather testily she replied, “It was fine!”
“Everything?” Chad asked, glad that she was at least speaking to him again. “How about where I changed the one form around.”
He was doing it again! Irritating her! Just like a stupid child! He had to have every little thing broken down so he could be praised for it. Well she wouldn’t! “It was all fine!” she replied even more angrily.
“You’re sure?”
Something inside of Robin broke then. She couldn’t take it. She couldn’t take his childish whining. His childish behavior. His childish attitudes. Her mind was now totally focused on her bag in her desk drawer and what was in it. Apologize? There was no way she could apologize to him now. He was nothing but a damn fool. A pervert! A stupid twisted child who never grew up. Heck! He even wanted to spend the rest of his life in diapers with no control over anything. Apologize? Not on her life!
Without realizing it, her pace increased as she continued back toward her desk. He tried to ask a few more questions, but she ignored every one of them, till finally he got the point and stayed silent. The idiot!
The moment she passed his cubicle, she stopped and turned. He was just about to go into his. She reached out and grabbed his arm instead. “This way,” she said as she turned and dragged him into her own cubicle. Once she was back at her desk, she released his arm. “Strip!” she commanded. “Right now! Completely! The only thing I want to see left on your body is your stupid childish diapers and those even more childish plastic pants!”
Chad was taken totally by surprise. Now what had gotten into her? What had he done wrong? Anything? He couldn’t think of a single thing. But there was no doubting the change in her attitude. She was definitely angry again about something. So once again he began removing his clothes in front of her.
Robin watched Sissy getting undressed for a few minutes, then she opened her desk drawer and pulled out her large bag.
Chad was once again down to just his diapers, plastic panties, and his waist cincher. Yesterday she had told him to leave the waist cincher on, but he wasn’t sure what she wanted him to do with it today? “How about this?” he asked as he grabbed the top of it.
“I said everything, didn’t I?” Robin replied testily. “Get it off!” It took a few moments, but eventually he was down to just what she wanted. “Finally!” She reached into her bag and pulled out something large and white. She threw it at him. “Put that on!”
Chad held up the garment she had thrown at him. It was a t-shirt – a woman’s t-shirt. And it was fairly big! But the worst part of it was what was written on the front. In big bold letters it said: “Baby” and then there was an arrow under that pointing down. It must have been something she had worn when she was pregnant – which also helped to explain why it was so extra large.
Robin watched as he put the t-shirt on, covering up the incongruous breasts that he couldn’t remove. She loved that fact that it said Baby on the front and the arrow pointed right down at his diapers… or it should have. The darn shirt was too long. She reached out and grabbed the shirt and knotted the bottom of it at the side. Then she stood back again. His childishly patterned plastic panties were now completely on display. She pointed at the floor. “Down!” It was the only word she figured she needed.
Chad dropped to his knees. Was she going to stick him under her desk again like she did yesterday? If so, then why make him take his clothes off?
“Now,” Robin said. “Where does your thumb belong?”
Chad brought his right thumb back to his mouth and started sucking on it like he knew she would make him. He just hoped she wouldn’t wrap tape around his head again today to keep it there. But the extra humiliation of his situation suddenly made him start peeing again without warning. He briefly berated himself for not watching more carefully for it so he could hold back. But he didn’t get to think about it long.
Robin nodded her head. “Much better! Now there’s no chance of anyone mistaking you for anything other than a pathetic stupid sissy! You can just stay there now and spend the rest of the afternoon playing like a baby on the floor.” She watched him staring wide-eyed back at her for a moment. “Oh,” she added. “We forgot to give you something to play with, didn’t we.” She reached back into her bag and pulled out a stack of papers she had printed from her home computer the night before. “I’m afraid this was the best thing I could come up with on short notice,” she explained as she removed the paper clip binding the papers together. She looked down at him on the floor with his thumb in his mouth, then at the papers in her hand. This wasn’t going to work out as well as she thought as long as he had to suck his thumb, but there was no way she was going to let him remove it! Still, she had to keep him occupied. She removed just the first page from the stack and handed it to him. No use giving him any more till he was ready for them.
Chad stared at the piece of paper she had handed him. Most prominently on it was a cartoon drawing of a little girl wearing nothing but some flowered panties. It took him a moment to realize that it was part of a cut-out paper doll system and the other pages Robin had were probably the clothes for the doll. He looked up at her questioningly. What was he supposed to do with it?
Robin opened her desk drawer and pulled out her scissors, but the moment she did, she realized that they weren’t right. You should never give a child scissors like that. They could seriously hurt themselves! But… it was all she had… for now. Reluctantly, she handed him the scissors. “Don’t hurt yourself with these,” she cautioned as if she was talking to a child.
Chad took the scissors with his free hand. He looked back at the paper in front of him and guessed that she wanted him to cut the doll out. He pulled his thumb out of his mouth so he could use two hands to do it.
“Keep that thumb in your mouth!” Robin ordered the moment she saw him pull it out.
Chad quickly replaced his thumb and looked up at her questioningly. How was he supposed to cut the doll out with only one hand – his left hand at that?
Robin smiled down at him, guessing the question that was going through his mind. “You’ll have to use just your one hand to cut that out. Maybe it will keep you busy for a while. Oh, and I suggest you try to do a very good job with it.”
With only one hand to use to both cut the paper and hold it, the job was impossible! Especially with only his left hand. But Chad had no choice but to try to awkwardly hold the scissors and set about the task. He propped the paper up against his leg as he sat on the floor and started working his way with the scissors into the paper. The task was extra hard because he wasn’t left-handed. As soon as the scissors touched the paper, it slipped off his leg and fell to the floor. He quickly realized that this was going to take him a long, long time. That is, if he ever managed to do it.
Robin sat down and watched him for a few moments. She felt very satisfied with herself. Maybe she was a bad person. She didn’t want to be, but maybe she was. Of course, there was the other thing that Gloria had suggested, that Sissy didn’t fit into the same little boxes that everybody else did. That he might not consider her to be bad at all. So was she bad? She didn’t want to be. But… there was no other way she could see to deal with him right now. So until she came up with something better, she would be… bad.
She almost laughed at the trouble he was having trying to cut that doll out. The task was pretty much impossible. She saw him look up at her briefly as he did it. In some ways, he reminded her so much of her baby son, sitting on the floor, playing, glancing up at her just to know she was still there… He did look so much more like a baby now. An overgrown baby to be sure, but still a baby. Nothing at all like a responsible adult – which he wasn’t! Now he was in his natural state – as far as she was concerned.
She turned away from him then to do some work, but working was once again out of the question. Instead she opened up her email program and began going through all of the emails she had gotten from Mel in the last few days, starting with Mel’s first one. She began taking notes on all the separate little things that Mel had suggested – which wasn’t much at all, but when added together seemed to amount to so much more. She already had him curtseying for her, but not every time he opened his mouth. She wondered how she could manage that one. She’d have to wait and see. She also had him using his sissy voice around her now, but Mel’s latest email had suggested that she had made some major changes in his voice that she hadn’t heard yet. She marked that one to check soon.
One other thing she took particular notice of was that Mel had told her in today’s email that he should have a pacifier with him. That was very interesting. She turned around to look at him. He was trying to turn the paper around to find another way to cut at it, but he was getting nowhere. Perfect busywork for him. But, would the pacifier be any better than his thumb? She did find it funny that he only had the use of his one hand. She decided that it couldn’t hurt to just try the pacifier – if only for a few minutes. “Mel says you should have a pacifier with you. Where is it?” she asked.
Chad looked up at her to answer and pulled his thumb out of his mouth. “It’s in…” But he got no further before Robin interrupted him.
“Wait a minute! Stand up!” She waited till he got to his feet. “Curtsey – and keep that thumb where it is!” She watched as he curtseyed. “Now take your thumb out of your mouth and answer me.”
“It’s in my purse in my desk drawer,” Chad said.
“Put your thumb back in your mouth again,” Robin ordered and waited till it was where she wanted it. “Curtsey again.” So darling! “Down!” She pointed at the floor. Something inside of her felt almost sexually stimulated by what she had just done with him. Hmm… That had actually worked out well!
She left him for a moment and dug his purse out of his desk drawer. She noticed as she went through it that it was as jumbled and disordered as her big bag usually was. Fortunately, the pacifier was easy to find. She put his purse away again and went back to him. “Here,” she said. “Stick this in your mouth instead.”
Chad was embarrassed over the fact that she had found his stupid pacifier and that he would now be sucking on it – in front of her – a work! But was it any better than his thumb? In his mind it was. The pacifier wasn’t part of his body, it was something made just for a baby. And now that baby object was where it was intended to be used – in his mouth. But at least he now had the use of both hands to cut out the doll. As soon as he saw Robin sit back down again, he started in on the task. So much easier!
Robin watched him playing on the floor. She saw him snip a bit closer to the doll. Then she watched as he lined up the scissors to begin trimming right around the outline of the doll. It was a tricky cut that he could never manage to do with only one hand.
She saw him look up at her again before he actually started cutting. Dressed as he was in just that stupid t-shirt which left his childish diapers and plastic pants on display, she was again struck by the resemblance between Sissy and her son – two babies that played on the floor. Of course, by now she’d be wiping the slobber off of her son’s face since he seemed to drool a lot – especially whenever he had a pacifier in his mouth. She sat up straighter and just stared at Sissy for a moment. So much like a baby! “Drool.” The word just seemed to pop out of her mouth.
Huh? Chad wasn’t at all sure what she had said. He looked up at her quizzically.
“I said drool! Like a baby.”
Chad wasn’t sure he heard her right. Drool? She had to be kidding. Not to mention, he wasn’t sure how he was supposed to go about doing it – especially with the pacifier plugging up his mouth.
“I said drool!” Robin repeated more urgently now.
But Chad still wasn’t sure what to do. And he still couldn’t believe her request.
“Stop swallowing whatever saliva is in your mouth and push it out through your lips instead. Drool!”
Chad was horrified! She had to be kidding… but she wasn’t!
“Now!” Robin ordered.
Chad searched his mouth for whatever moisture was in it, which was surprisingly a lot, and did his best to push it out between his lips with his tongue. But the pacifier made the action difficult. A little bit did escape though. It felt horrifyingly weird as it started to drip down the length of his chin. He automatically reached up with the back of his hand to wipe it and keep it from dripping.
“Don’t!” Robin ordered. “Let it drip. In fact, drool more. I want to see your chin covered in slobber!”
Chad was nearly shaking with humiliation as he did his best to let a little more drool out of his mouth without losing the pacifier from between his lips. Again, he felt the tickle of it dripping down his chin.
“More!” Robin ordered. “Lots more! I want to see tons of slobber dripping down.”
Very gradually, Chad did his best to try to push all the moisture out from his mouth. He could feel it starting to drip off of his chin now so he held one hand up under him to catch it.
“Don’t bother!” Robin told him. Just let it drip!”
The entire mouth guard around the pacifier in Chad’s mouth felt horribly wet and messy. His entire chin was wet now soaked. It felt awful. He felt – hugely embarrassed. And of course, that was the moment that the stupid suppository that Cassie had put up into him earlier decided to do its thing.
Robin sat staring at him, totally fascinated by what she had just made him do. So much more infantile – it was ridiculous! He was ridiculous! And then she noticed the embarrassed expression on his face change to something else. She saw him raise his bottom up off the floor like something was wrong. “What is it?” she asked.
All Chad could do was to look up at her from the floor, his slobber covered pacifier in his mouth, his chin dripping with drool. A tear was forming in his eye. He just turned his head toward his backside for a moment.
“You mean, you’re messing yourself – again? Just like yesterday?”
Chad only nodded and hung his head as he leaned his body forward to make it easier for the mess to get out of him. For some reason, it wasn’t coming as quickly or as forcefully today as it usually did, so it took much longer. But the results were still the same. A few minutes later, he was stuck with a load in his already wet diapers, and he was going to have to sit down on that mess. Ugh!
Robin laughed. Not out loud, but she still laughed. God, what a freak! She still couldn’t believe him! Such a pervert! There was no way at all that she could look down at the idiot sitting on her cubicle floor and see the old Chad or even Chad who she once thought wanted to be a woman. In fact, there was no way she could see anyone who she could consider an adult – or even deserved the respect of an adult… or another human being for that matter. What sat on her floor was… a sissy. It was the best description she could think of for him.
“You keep drooling like that!” she told him in no uncertain terms. “I don’t ever want to see your chin without fresh slobber all over it.” She laughed again at him. Well, he deserved it!
She tried to compare him again with her son. With his chin full of slobber, the comparison was more noticeable. But now she realized other differences. For one thing, her son was all boy. He loved playing with cars and trucks. Whereas Sissy, well, she supposed that sissy should only be playing with girl things. Hence, the paper dolls she had found for him. While not exactly a baby toy, they were the best she could do last night. Still, she really liked the idea. She wondered if there was some way to make him look a bit more like a girl than a boy. Maybe a big bow in his hair? She’d have to think about that one.
She thought of something else too. Her son was one year old now. He was not only walking, he was running – everywhere. She had already been thinking in the back of her mind about when she could start potty training him. She now made that decision to start tonight! She laughed again. Once her son was potty trained, he would be more of an adult than Sissy!
And then she caught a slight whiff of the odor from Sissy’s diaper. Without everything else to cover it up and keep the odor in, he was going to smell – like a dirty baby. That realization sobered her. Ugh! But no matter what, she was going to keep him on the floor just like that till she left to go home. The idiot! Ugh! Why didn’t she pack some air freshener in her bag this morning?
She pulled out her cell phone and asked him to look up at her. She snapped his picture. She was pleased to see that the camera in her phone had picked up all the details from the arrow on his chest pointing down at the childish print on his plastic pants, to the shiny slobber all over his pacifier and chin. Picture of an idiot! She emailed it to her work address so she could access it from her computer. A minute later, while he was still cutting out the doll on the paper, she was writing an email to Mel to send the picture… along with a few little requests.

The Bet - Chapter 48 (Thursday – week 7 Part 4 of 7)

The Bet
by Karen Singer

Chapter 48 (Thursday – week 7 Part 4 of 7)

“How’s that look?” the beautician asked as she held the mirror up behind Mel’s head so she could see the back of her hair.
“Good,” Mel replied. “That’s more of what I want.” She had just taken a few minutes to come in and get a long overdue haircut. Just trim the ends and neaten everything back up again. One day she would actually find the time to get the style changed, but this wasn’t that time.
Once she was out of the chair, she headed up to the cash register to pay. As she handed over her credit card, she noticed the nails on the girl who was the cashier. “Oh, that’s different,” she said as she stared at the girl’s nails. Pleased, the cashier held both her hands out so Mel could see her pretty nails. Mel finished paying for her haircut, but as she was walking back out to her car, she already had her cell phone in her hand and was dialing her usual nail salon.

Chad was once again back at work on the project. It was nice to have nothing to do once in a while, but overall, he’d much rather be busy. And the things he was doing right now were the kind of things he was particularly good at. While Robin may be a lot better than him with some of the art and design ideas, he was still more proficient in the technical areas.
Since they each had returned from lunch, Robin had yet to say a word to him or even acknowledge his existence. She hadn’t even spoken to him since earlier when she had assigned him the work to do. In a way, he was glad, but he’d still like her opinion on a few things once in a while. But asking her opinion was out of the question. He wasn’t about to make her angry by going over to talk to her for something as minor as that. Still, it would be nice to know if she had a problem with anything he was doing.
He finished another small portion of what he was working on and stopped for a minute. He didn’t know what Robin was doing in her cubicle on the other side of the wall, but for now, everything seemed quiet enough. He opened up his spreadsheet for keeping track of the bet. Still fifteen days to go before the testing. Almost down to two weeks. Once again, it felt like both a long time and a very short time to go.
In the time since the bet had started, everything had changed so much. Incredibly much! Things that seemed normal to him now were unthinkable such a short time ago. It was unbelievable how much his life had changed… how much he had changed. And what about when the bet was over, after he had won? What then? Would people ever see him as the same old Chad he used to be? Probably not. Maybe after a few years, but even then they would always remember him as he was now… a sissy. Like it or not, he would have to deal with that. He was forever branded with it now and there was no hiding it. The best he could hope for was to minimize what everyone knew… because he had a feeling his life would be far worse if certain things ever got out.
He put the computer curser into the column next to yesterday’s date. How long had he managed to hold back? The day before it had been six minutes, up a minute from the day before that. But yesterday he hadn’t managed to make it to six minutes. He had gotten close, but despite trying hard, he just hadn’t gotten there. So he was going backwards again. But only by a little bit. Maybe today he could make it to six minutes again… or better! He was trying again, but so far it was tough going. But then, the afternoon had just started so he was hopeful. Rather sadly, he filled in five and a half minutes next to yesterday’s date. Down another half a minute. He had to do better!
Without bothering to look at his reasons for winning the bet, he closed the spreadsheet again before Robin could see it.

Robin was doing nothing. The project was open on her computer, but she had done nothing else with it. She could hear the faint sounds of Sissy typing on his keyboard on the other side of the wall so she assumed he was working on the project. He better be! Actually, she was sorry to admit that it was he who was now keeping the project on track since she herself hadn’t done anything with it all day… and really hadn’t done much with it since it started. So as much as she hated to admit it, she was glad he was working on it because she still wasn’t capable.
The only thing her mind wanted to think about was the talk she had had with Gloria over lunch. That hadn’t worked out at all like she had hoped it would. The darn woman wouldn’t ever come out and say anything one way or another! It was so infuriating! Really, all Gloria did was to take her own words and twist them around and throw them right back at her again. Darn her! But in doing so, she now had new things to think about. New ways to look at everything.
She wanted to be in charge, but the best thing for someone in charge to do was to let those under them do the work. She thought about that. She had no doubt that Mel probably had him doing all sorts of work for her. So when she thought about things in that light, she felt much better about Sissy helping with the project now. Of course, that didn’t mean that he had to take credit for all of it… any of it for that matter. After all, shouldn’t the credit go to the one in charge? So Sissy working on the project now was a good thing. But that didn’t mean that she wouldn’t be putting her marks on it too!
And then there was the other thing. Her main problem. She wasn’t that kind of person! She wasn’t a bad person at all! And she didn’t want to be! But damn him, Sissy didn’t fit into any of those little boxes that Gloria had talked about. He was outside of… everything! She couldn’t deal with him like… like… like a normal human being. He was… weird! Or different. Maybe they amounted to the same thing.
So was she being a bad person if she ordered him around, made him suck his thumb, made him sit under her desk? She didn’t want to be a bad person. She didn’t want to be cruel. But was it cruel… as far as he went anyway? She’d never even consider it with anyone else… anyone – normal. But, he wasn’t normal. So was it cruel?
With a groan, she realized she was thinking in circles and wasn’t really getting anywhere. Or at least she wasn’t making any decisions. Frustrated, she tried to force herself to go back to work again. But even though she somewhat succeeded at first, a little while later, thoughts of the items she had in her big bag began creeping into her head. And they were difficult to ignore. Was she bad? She didn’t want to be.

“So how did it go?” Mel asked as soon as Gloria picked up her phone. She had tried several times to reach her, but their schedules weren’t always compatible.
“I can’t tell you that,” Gloria replied.
“You can’t?”
“I’m taking you up on your offer to pay for the consultation, so I’m not allowed to tell you.”
“That’s not fair!”
“Sorry, but that’s the way it is. I can tell you though that everything she talked about was things you can probably guess. But I’m not saying anything further about it!”
Things she could guess? Mel figured she could guess a lot of things. But she knew nothing. And knowing Gloria, she wouldn’t even tell her if she needed to be worried about anything or not. But then she had to understand, she herself had her own non-disclosure rules she had to follow. Gloria was not going to be any help as far as Robin went. “I understand,” she finally replied – although disappointedly. She switched subjects. “So how about tonight? Are you going to hypnotize him again for me?”
“Do you still need me to?”
“Definitely. And this time, I really need to know how long he’s holding back – front and rear! It’s important. Very!”
“Since I told you I would keep doing it, then I will. No problem.”
“Great! We’ll see you at our regular time.”
“Good,” Gloria replied. “See you then.”
“Oh! Gloria,” Mel said before she could hang up her phone. “This Sunday, I’m going to try to have another little get-together at my place. Sissy is cooking – and he really is good. Won’t you come this time?”
“Sorry Mel. I told you before, not till this bet thing is over between you two. Then maybe I’ll think about it.”
“Okay, I just thought I’d ask – again.”
“It’s okay. You know I’m just trying to stay out of things.”
“Yeah, I understand.”
As Gloria hung up her phone, she briefly thought about one thing she would never admit to… she could have steered Robin in any of several directions today, but the one she decided to choose was the one that she felt would be best for everyone – including Mel.
Mel hung up her phone. Gloria still didn’t want to come to dinner. Or was it more like she didn’t want to see Sissy in his natural setting… under her thumb.
The knocking at her door broke her train of thought. “Come in, Andrea,” she called.
Andrea entered with her inevitable stack of papers. “Here’s the latest for you,” she said as she set the stack on Mel’s desk.
“Thanks, Andrea,” Mel replied offhandedly. Andrea was almost out the door when she stopped her though. “Andrea…”
“Yes?”
“I’m trying to plan another little dinner at my place Sunday night. Do you want to come?”
Andrea suddenly giggled. “And get to see what you’re doing with Sissy? You bet!”
Mel smiled. “Good! Plan on it then!”
“I will,” Andrea replied. “Thanks.”
One down, Mel thought. Now she just had to see if Sandy and Cassie could come – which she was fairly certain they would. Those two were usually looking forward to their Sunday dinners now.

The Bet - Chapter 48 (Thursday – week 7 Part 3 of 7)

The Bet
by Karen Singer

Chapter 48 (Thursday – week 7 Part 3 of 7)

Robin spotted Gloria waiting just outside the door to the restaurant as she walked up from her car. “Hi,” she said politely. “I really appreciate you meeting with me like this. Were you waiting long?”
“No, I just got here,” Gloria replied as they went in through the door. “Good timing.”
A few minutes later, they were seated with menus on the table in front of them. Gloria was there often so she didn’t bother opening hers, instead she waited patiently while Robin briefly looked over her menu before closing it. “So, you wanted to see me?” Gloria asked.
Robin felt bad and frustrated about asking for help, but she was here now. “Yeah,” she replied. “It’s just that…” But it was difficult to put into words what she really wanted to say? “That… I don’t know what to do about Sissy!” she blurted out. “I mean, he just makes me so mad!”
Gloria already had no doubt that Sissy was really at the heart of the matter, but all she did was to raise an eyebrow and repeat the word, “Mad?”
“Yeah! And the last few days I’ve started making him… I mean…” But she didn’t know how to say what it was that she wanted to say, so her main piece of frustration forced its way out of her mouth instead. “I’m not a bad person!”
Gloria was a little surprised by her sudden turn in the conversation, but many of her clients were often all over the place with their thoughts, so this was nothing new to her. All she said was, “You’re not?”
“No! I’m not! At least, I don’t want to be.”
“So you think you are.”
“No… I mean, yes… I don’t know!”
“So you think you might be bad. Why is that?”
Robin felt a bit embarrassed by her thoughts. “Because of some of the things I’ve been making him do.”
Gloria really wasn’t all that interested in knowing about it, but this was a professional consultation so she had to ask. “And what did you make him do?”
“Not much, at first,” Robin replied after a moment of reflection.
“At first? It’s only been what, two days?”
Robin blushed. “About that,” she mumbled. “I mean I made him…” She shook her head. “He was just being so childish!” she blurted out in her frustration. “So I made him suck his thumb.”
“You…” But Gloria didn’t get any further before Robin continued.
“And the second time, I taped it to his mouth so he couldn’t take it out without me knowing about it.”
“You taped it?”
“Well… I can’t trust him! He’s so damn childish! I just don’t know why I never saw it before. I mean he really is!”
“Childish? In what way?”
Robin shook her head. “He’s forever trying to get away with stuff. He tells half-truths. And when he wants something, he nags, nags, nags, just like a child. So… I treat him like one.”
Gloria took that in for a moment before saying, “I see. So you punish him.”
“Yeah. I can’t help it. He just infuriates me so much! Why didn’t I see it in him before?”
Gloria ignored her question for a moment and instead asked. “So you don’t… dominate him like Mel does?”
“Well, that’s just it, I’ve started doing a little of that too. A little.”
“But mostly, you punish him for being childish. Is it possible you’re more sensitive to his childishness now because you now know what he is?”
Robin thought about that, then sheepishly nodded. “But I don’t want to be bad!”
“And who says you’re bad?”
Robin was saved from answering right away by the waitress taking their order. When she left, Gloria pushed the question again. “Who says you’re bad?”
The answer seemed perfectly obvious to Robin. “Everyone!”
That surprised Gloria. “So you’ve told others about what you’re doing, and they’re all condemning you for it?”
“No, not that. I haven’t dared tell anyone!”
“So who says you’re bad?”
“Well wouldn’t anyone say that? It’s obvious, isn’t it?”
“Obvious, because you punish him for being childish?”
“Well, yeah, I guess. And for the other stuff too.”
“The other stuff?”
“Well, I’ve been making him curtsey when he sees me like Mel does, and I told him to always use his sissy voice around me too.”
“So you like dominating him?”
“No, it’s just that… it helps to remind me what he is all the time.”
“What he is? And that is?”
“A sissy of course!”
“Of course. So you feel you have to dominate him to help remind you of that, and now you’re feeling guilty about it.”
Robin nodded. “Something like that.”
“So you think that making him talk funny and curtsey once in a while makes you a bad person.”
“Well… there’s more,” Robin replied sheepishly. “Yesterday when I taped his thumb to his mouth, I made him sit in the corner under my desk for several hours. I told him it was his time-out spot for acting so childish. And then today… Well, I didn’t really do much with him today. I chickened out with what I had planned and tried to avoid him as much as possible instead.”
Gloria was a bit startled, but she didn’t let it show. She had heard worse. Much worse! “You chickened out?”
“Well, yeah. I had this idea last night, but this morning I realized that everything I was doing was wrong. All wrong. It’s not right!”
“Not right as far as you’re concerned, or Sissy?”
That startled Robin. “It’s just not right! Period!”
“So don’t do it.”
Robin shook her head. “You don’t understand. I can’t deal with him like I used to! His childishness makes me so angry I just want to kill him!”
“So dominate him.”
But I can’t! It’s all wrong.” Robin leaned forward to emphasize her words. “I’m not a cruel person. It’s not me!” She leaned back again before continuing. “All I ever wanted to be in life is a wife and a mother. And now I am. I’m not some freaky dominatrix person with a whip and boots and… well, you know. I’m not a cruel person. It’s not me.”
“It’s not you, or not what you think you are.”
Robin had to think about that. “It’s not… I’m not…” She shook her head. “I don’t know. Every time I see him I still get so mad at him. And it’s been almost a week now since I found out!”
Gloria nodded. “You’re angry at him and you can’t let go of it.”
“Yeah! Exactly.”
“And you’re frustrated about it.”
“Yeah!”
“So what is it you want to do?”
Robin shook her head. “That’s why I’m here. I don’t know!”
Gloria nodded. It was time to backtrack a bit. “So now because you’ve made him do a few things you’re afraid that you might be a bad person.”
Robin wasn’t sure, but she thought that Gloria might be twisting her words a little. “Kind of,” she admitted. “But it’s not me! I’m not a bad person.”
“I didn’t say you were.” Gloria paused to think for a moment. “You say you’re not cruel. Was it cruel to tape his thumb to his mouth? Was it cruel to sit him under your desk?”
Robin nodded. “Yes, it was. I need to apologize to him for that I guess.”
“Maybe. But… was it cruel by your standards, or his?”
“Huh?
“Do you think that Sissy thought it was cruel to have his thumb taped to his mouth?”
“Well sure. Wouldn’t he?”
“I don’t know. He’s a sissy. And his particular breed of sissy craves that kind of thing.”
“So I wasn’t cruel?”
Gloria shrugged. “It depends on whose standards you’re going by.”
Robin was a little startled by that. “Whose standards?” she repeated. She paused a few moments while she tried to figure that one out. “So I wasn’t being cruel when I made him do those things?”
“I didn’t say that.”
Robin was getting more confused. “So I was being cruel.”
“I didn’t say that either. It depends on whose point of view you want to go by.”
Robin was getting more frustrated now. This just wasn’t working! “Whose point of view? Either I’m wrong, or I’m right! Either I’m bad, or I’m not!”
“I’m afraid that it’s not really that easy,” Gloria replied. “You say your big problem is that you can’t deal with him as you now know him to be, yet you have been dealing with him – the best way that you can.”
“But it’s all wrong! I’m not that kind of person!” Robin protested.
“But you’ve been dealing with it – as that kind of person. You’re just conflicted because everything you’re doing goes directly against everything you believed – before! But now you’re finding out that life isn’t that simple. Life doesn’t always fit into nice neat little boxes. Sometimes you have to find a different way to deal with something, even if it doesn’t fit into one of those nice neat little boxes you want your life to be ruled by.
“You say you’re not a cruel person. But again, cruel by whose standards? Yours? His? Or do you need to look somewhere in the middle. Make some concessions in your life that will enable you to deal with him in a way that satisfies your needs – while at the same time, keeping in mind that you can look a little bit out of that box you want to put him in because of his own ‘unique’ point of view of life.
“Let’s face it,” Gloria continued, “he’s a bit different. But he has needs just like you and I do. His needs are just a bit…” she searched for a good word.
“Weird!” Robin finished for her.
Gloria smiled. “Maybe. But you’ve got the idea.”
“So what I’ve been doing is not wrong?”
“I’m not saying that.”
Robin grunted and rolled her eyes. “You wouldn’t, would you! You won’t say one way or the other.”
Gloria leaned forward. “Only you can answer that one.”
Robin had to pause for a few moments to calm down and think. She was getting frustrated by Gloria’s non-help. “It helps me to see him as a sissy and not as… Chad… or even as Chad who was trying to be a woman.”
“Why is that?” Gloria asked.
“Because every time I see him in those… more normal roles, I can’t help thinking that this… decent person, is nothing of the sort! He’s perverted! He’s twisted! He’s… an idiot! Can you imagine, wanting to go around wetting yourself all the time. Not to mention messing himself too! God! What a jerk! It makes me so mad I could just shake him! And he’s going around trying to act like he’s totally normal? Not warning anyone at all that in reality he’s a damn… pervert? God, it just makes me so mad!”
“But is he a pervert?”
“By my definition he is!” Robin replied.
“But you said that’s how you see him when he’s in a ‘more normal’ role. What else is there?”
“His sissy role.”
“What’s the difference?”
“The difference? He’s not running around pretending to be something he’s not. He’s not trying to fool anybody into thinking he’s normal.”
“And it doesn’t bother you to see him in that light, as a sissy?”
“It bothers me, just not the same as it does when I try to see him as a normal person. I can see what he is, and it kind of triggers something in me that says I can deal with him differently. If I don’t see him as a normal person, then I don’t have to deal with him as a normal person. But when I see him in any kind of way that even ‘might’ be normal, then I just get confused and angry and everything seems all wrong.”
“So it’s easier for you to accept him as a sissy, than as someone… normal.”
“I don’t know about accept him, but I can deal with him.”
“So you have no trouble dealing with his as a sissy.”
“Yeah, I do have trouble. But when I see him that way, every time he makes me mad, I just have to find some way to punish him, and then I feel better about it.”
“Better about it?”
“Yeah. Well, maybe more… justified anyway.”
“But you can deal with him that way.”
Robin nodded. “Yeah, I guess.”
Gloria just nodded. “And now you think you’re bad because of the way you want to deal with him.”
“Well, I guess I am,” Robin admitted.
“Again, by whose standards?”
“What does it matter?”
“To some people it might.”
Robin had to think about that, but only for a moment. “I guess, by my standards.”
“Good,” Gloria replied. “That’s important! So what you need is for Sissy to fit into your little box of acceptable standards?”
Robin was thrown off balance. First Gloria had praised her, then in the next breath she had pulled the rug out from under her again. “Him fit into my standards?” She thought about that for a moment. “I wish!” She looked at Gloria for a moment. “I guess I can’t expect him to fit my standards, can I? At least… not anymore.”
“As I said, he has needs too. And his needs make him see life a bit differently than you do. While he’s very aware of what most people would consider ‘normal’ or even ‘acceptable,’ his needs force him to make room for something more. He knows he doesn’t fit in, even when he tries.”
“Yeah, I get it,” Robin admitted sullenly. “But that doesn’t make it right!”
“Again, for you? Or him?”
Robin looked at her for a moment. “I guess, for me.”
“But to him it may be okay?”
Robin nodded. “I guess.” She remembered something then. “Yesterday, when I told him that I didn’t know what the bounds were on this type of thing, he told me that there were no bounds. I could do anything!”
“That may have been a bad choice of words on his part,” Gloria replied. “I’m sure he has bounds. He just may not have reached them yet.”
Robin nodded. “Yeah, probably. But maybe it means, that he doesn’t really mind what I’m doing to him all that much. Maybe, no matter how much I feel that it’s wrong, he doesn’t.”
“Possibly,” Gloria admitted.
“But it still feels wrong,” Robin replied.
“And it is! To most people! And also to you because you’re matching it up against how you treat everyone else.”
As Robin tried to digest that, their food finally arrived. When the waitress had left, Robin stuck a French fry in her mouth and said, “I’ve been trying to avoid him as much as possible so I don’t have to see him and get angry again.”
“How’s that going?” Gloria asked with her mouth full of hamburger.
“Not so well. We work together, and now our boss has thrown us together on another project.” She looked up at Gloria. “I could handle the whole project by myself! There was no need for Tom to include Sissy in it too!”
“In other words, you just wanted to avoid him.”
Robin nodded before she stuck some chicken in her mouth. “Yeah, I guess. The less I see of him, the better. The problem is that I really can’t avoid him.” She thought of something else. “The one little piece of advice that Mel gave me was to make him understand that I’m the one in charge of everything now, not him.”
“And?”
“So, since I don’t really need his help on this thing, then I’m not letting him touch it.” She rolled her eyes before adding, “which means he has nothing to do and so he seems to find ways to act more childish again and make me mad at him.”
Gloria had been about to take another bite of her hamburger, but she delayed it. “That’s a twist,” she said. “You want to be the boss – and do all the work too – while your workers, or in this case worker, does nothing.”
“But I don’t need him!”
“I didn’t say you did. It just struck me as different. Not wrong, just different.”
But her words struck something in Robin that made her think about it. “You’re right, the boss doesn’t do all the work. He makes everyone else do it for him.”
“Maybe not exactly like that,” Gloria replied. “A boss still has a lot of responsibilities, they’re just different responsibilities. Not less, not easier, just different.”
Robin nodded. She had a lot to think about. It was still all wrong! But was it really? And the one in charge doesn’t have to do all the work!

The Bet - Chapter 48 (Thursday – week 7 Part 2 of 7)

The Bet
by Karen Singer

Chapter 48 (Thursday – week 7 Part 2 of 7)

Robin moved her mouse a little, then clicked it, trying to get some work done. But her heart wasn’t in it. As much as she tried to work, her brain was too preoccupied with feeling bad over what she had done with Sissy. Even this morning! It wasn’t right! It was all wrong! It was the very things she had been mad about in the first place. Mostly. But it had been like she couldn’t help it! Curtsey for her every morning to greet her? Ridiculous! And now she felt bad about demanding it. But should she go apologize to him? With as mad at him as she still felt, she just couldn’t do it.
So what should she do? With a frustrated sigh, she gave up all pretense of working. She wasn’t getting anything accomplished anyway. What was he doing over there on the other side of the wall? She knew he wasn’t working on their project. She wouldn’t let him! He was probably wasting his time searching the internet instead of doing something useful… like trying to learn something new to use here at work. Or at least stay up on the latest trends for their job. But somehow, she doubted that he was doing anything except goofing off – like a child!
So what was she going to do? She couldn’t think! Especially with him so close – right in the next cubicle. She needed to get away! Go somewhere else to think! Frustrated, she got up and headed out. She paused only slightly as she passed Sissy’s desk. Her quick glance showed her pictures on his screen, but she never paused long enough to really see what they were. But pictures weren’t work related, so just as she guessed, he was goofing off! Not that she really cared. Just as long as he didn’t touch their project without her say-so!
Not knowing where to go, she wandered the hallways as she tried to think. But no answers were coming to her. Eventually, she found herself in the break room, which was empty. She did notice that the coffee pot was filled and ready so she poured herself a cup and took it over to the women’s usual table. She sat and nursed her coffee for a long time while she pondered what to do.
If only she had someone she could talk to about it. Someone who could help without thinking she was crazy. She certainly couldn’t talk to Mel! Mel was the last person she’d want to talk to. But thinking about Mel reminded her of Mel’s friend Gloria. She had made more sense than anyone she had talked to in a while. She wouldn’t mind talking to Gloria – but it would have to be without Mel! And Gloria was Mel’s friend! So she was left with nobody to talk with at all.
She sat and nursed her coffee, no solution coming to her. But she didn’t leave. Eventually, she watched as a worker came in with two boxes of doughnuts and set them out. Then the worker checked the coffee to make sure there was enough. Then the worker left, and she was alone again. But only for a few minutes. Two men came in and headed for the coffee pot. They were the first ones to arrive for morning break. She got up and refilled her cup, grabbed a doughnut, and sat back down again. No answers. Nothing.

Chad glanced at his clock. It was break time, but where was Robin? He had thought he heard her leaving a while ago, but as far as he could tell, she never came back. He got up and went to her cubicle. She wasn’t there. Puzzled, he headed alone for the break room.
He was nearly in line to get coffee before he spotted her at their usual table. She already had her coffee. He wondered where she had been. He got his own coffee and one of the doughnuts and carried it over to the table. There was no seat open next to Robin so he took one a bit further away. All through break, he noticed that it looked like she wasn’t paying much attention to what was going on at the table – like she was thinking about something else. The few times anyone spoke to her, she gave mostly short answers that didn’t really say anything.
Robin was mostly annoyed anytime someone spoke to her, mostly because she hadn’t been paying attention so she had to try to remember what had been said. Fortunately, nobody really talked to her much. She was glad that for once Sissy wasn’t sitting next to her. He was her main problem. She just didn’t know what to do about him.
It wasn’t till break was nearly over that the idea hit her. It wouldn’t solve her problem at all, but maybe… maybe… she could at least get her own thoughts and fears figured out. Suddenly, everyone was getting up to go back to work. Good timing! She got up right along with them and headed back to her desk. She knew Sissy was following her, but fortunately, he wasn’t saying anything. She didn’t acknowledge his presence in any way, not even when she got back to her desk.
But working right now was not her first priority. She grabbed her phone and dialed Mel’s number… and started walking down the hall with it, away from Sissy. But she didn’t get through to Mel, she only got as far as Mel’s receptionist, Andrea.
“Mel just went in with a client,” Andrea said into the phone. She recognized Robin’s name as one that Mel wanted to be told about immediately if she called. But still… “Can this wait till she gets out or do you need me to get her now?”
Robin felt a bit of frustration. Mel was busy! It figured! But... “No, it can wait… a bit. But not too long I hope. Can you have her call me?”
“Absolutely! As soon as she finishes. Um… I estimate about half an hour. Will that be alright?”
“Sure,” Robin replied. “That’s fine. Thanks.” She hung up the phone and headed back to her desk. Half an hour. Not long, but still an eternity. She tried to fill the time by working, but she simply couldn’t concentrate on the job that needed to be done – which only added to her frustration. Ugh! She was falling further and further behind on the project!
She thought about Sissy, just on the other side of the wall, doing nothing! Nothing! And that fact irked her! And so did the sinking realization that she could put him to work, get him to help. Let him do what she wasn’t capable of doing today… just so the project could get back on track. Damn him! “Sissy!” she called over the wall. “Get in here!”
Chad nearly fell out of his chair at the unexpected summons. He quickly went around to her cubicle and curtseyed as he entered. “You wanted me?” he asked.
Robin actually winced at his curtsey. It wasn’t her! It wasn’t right! But she said nothing about that. “I need you to do some work for me,” she told him. She spent the next five minutes explaining what she wanted, then kicked him out again. And again she mentally winced as he curtseyed before leaving. She really needed to put a stop to that!
Chad was elated. She had found some work for him to do. Real work! Work where he would be making a definite contribution to the project. He wondered what had changed her mind… not that he was going to ask. As far as he was concerned, he was going to do everything possible to stay out of her way – completely! He quickly closed his internet browser and opened the project instead. Down to work!
Robin stared at the entrance to her cubicle where Sissy had disappeared from only moments ago. She felt guilty – for a number of reasons. She felt guilty for treating him badly. She felt guilty for not including him in the project so far, and now she felt guilty about making him work because she couldn’t. It wasn’t right. But she could do nothing about it. She glanced at her clock. Still fifteen minutes till Mel would call – probably. If Mel called.
Not wanting to sit at her desk again, especially now that she could hear the faint sounds of Sissy working on the other side of the wall, she grabbed her cell phone and began wandering the hallway’s again, but this time she didn’t go near the break room.

Mel walked her client to the door and shook hands with him. Then she turned and headed back toward her office.
“Robin called you,” Andrea told her as she passed her desk.
Mel was more than a bit surprised at that. “She did? What did she want?”
“She didn’t say other than she wanted to talk to you. I got the impression she wanted to talk sooner rather than later.”
Mel nodded. “Okay, thanks. I’ll call her right away.” She went back to her office and found Robin’s number and called.
Robin jumped when her phone suddenly rang. “Hello?” she said quickly.
“Robin?” Mel’s voice came through. “How are you? What can I do for you?”
Robin sighed before answering. Where should she start? “Um… I really hate to ask this,” she began.
“Anything,” Mel replied quickly. “And don’t be afraid to ask.”
“Well… You know your friend Gloria that I talked to at lunch the other day?”
“Yeah.”
“Well… Do you think you could call her and ask if I can meet her for lunch again?”
Mel was surprised by that. “Of course. In fact, you can join us anytime you want. We’d love to have you.” Actually, she wasn’t all that sure how Gloria would feel about it.
“Well… that’s just it. I mean… I don’t want to be rude or impolite, but… Um… I was really just hoping I could talk to her myself. You know?”
Mel did feel a bit put out… but under the circumstances… “Sure,” she replied as cheerily as she could. “I’ll call and ask her, then let you know. Okay?”
“Thanks Mel. I appreciate it. A lot!”
“Is everything going alright with Sissy? Is there anything you need me to do?”
“Oh no! Like I said, I really would just like to talk with your friend Gloria again. Please.”
Mel realized that Robin wasn’t going to tell her anything about what her problem was. “No problem. Like I said, I’ll let you know as soon as I talk to her.”
“Thanks again Mel,” Robin replied. She felt somewhat relieved, but only somewhat.

Mel hung up her phone. Robin wanted to talk to Gloria. Alone! She wasn’t sure how happy she was about that, but at least Robin hadn’t started yelling at her again. She picked up her phone and dialed Gloria’s number.
Gloria was just about to go into a session with one of her few morning clients when she heard her phone ringing. She quickly motioned to her client that she would be just a moment, then she answered the call.
“Hi Gloria,” Mel said. “I need you to do a favor for me.”
That didn’t exactly sound like the kind of thing that Gloria had on her list of things she most wanted to do. “What is it?” she asked. “I’ve got a client waiting.”
“Robin just called me. She wants to meet with you for lunch.”
Ugh! Just what she needed. “Do you mean just me, or both of us?”
“Just you.”
“I was afraid of that. You know I usually get a lot of money for things like this.”
“I know. But I figure that if she’s got a problem, then it’s my fault to begin with, so I’m responsible for it. So bill me for it. In fact bill me for both of your lunches too.”
“You know I was just kidding,” Gloria replied.
“But you also know me better than that. Bill me.”
Gloria shrugged. “Why not? Okay, tell her I’ll meet her outside our usual place.”
“Thanks Gloria. I appreciate it.”

Robin was still heading back to her desk when her phone rang again. That was quick! “Hello?”
“Hi Robin. I just talked to Gloria. She said she’ll meet you outside the restaurant where we had lunch the other day. Is that okay?”
“Wonderful!” Robin replied with relief. “And I’m so sorry about this. It’s just that… Well… Never mind. I just appreciate it.”
“No problem. Let me know if there’s anything else I can do for you.”
“I will. Thanks Mel.” Robin felt much more relieved as she returned to her desk. Gloria had made so much sense when she had talked with her. But the question now was, would Gloria be able to help her this time? She could only hope.

Mel stared at her phone for a few moments after she finished talking with Robin. She desperately wondered what Robin’s problem was… and she was sure there was some kind of problem because why else would she want to talk to Gloria?
But since she was fairly certain that Robin’s problem was related to Sissy, she was reminded of one other little technical thing she had to arrange for Sissy now. She picked up her phone again and called Cassie’s number. She listened to the phone ringing for a few moments and was about to give up when she heard Cassie breathlessly answer it. “Hi Cassie. It’s Mel.”
“Hey Mel. What’s happening?” Cassie asked.
“It’s time to make a little change again in Sissy’s suppository routine.”
“Okay, no problem. What do you need?”
“Don’t put any more up into him at lunch time from now on. I’ll continue to give them to him at night once in a while. But that’s being cut back too. I just need you to make sure he keeps thinking you’re giving them to him.”
“You think he’s ready for it yet?” Cassie asked.
“As far as I can tell he is. Besides, it doesn’t matter much. We’re running out of time and I have to stay on schedule.”
“Okay,” Cassie replied. “From what I’ve heard, he doesn’t have a clue anytime we do it or don’t do it.” Another little thought hit her. “Cindy isn’t going to like it though, because it means I can’t let her change him. I don’t want to take any chance that she might ‘spill the beans’ so to speak.”
“Well, it won’t be for too much longer anyway. Just the rest of this week and next week. After that, he’ll be with me all day.”
“Okay,” Cassie said. “No problem.”

Chad headed slowly toward the gym doors. Yesterday, Cassie had taken care of him. But the way things were going lately, he was betting that this time it would be Cindy, the receptionist, who would be doing it. When Cassie changed him, she played with his backside, giving him the most wonderful feelings in the world. Almost like regular sex. He just wasn’t able to orgasm from it with her… yet. He couldn’t wait to keep trying though. But today, if Cindy took care of him, then he had no idea what would happen – other than she would change his diaper. Oh yeah, and stick another stupid suppository up his butt. Ugh!
Bracing himself for Cindy, he opened the gym door and went inside. The first thing he noticed was that Cindy didn’t look as excited to see him as usual. Or maybe it was just his imagination. But that all changed when she leaned across the tall desk and smiled at him. Wickedly? He started bracing himself for the worst. But she was just staying right there, not moving, not saying anything. Waiting? Ugh! He curtseyed and said. “Hewwo, Cindy,” in his sissy voice – his old sissy voice. He was rewarded to see her smile broader and stand back up again.
“Hi Sissy,” she replied. But she didn’t say anything else or even offer to go find Cassie.
Chad saw her just standing there as if she was waiting for something again. “So are you going to be changing me again today?” he asked tentatively.
Cindy’s face brightened somewhat. “Would you like me to change you today?” she asked hopefully.
Chad wanted to be changed, he just would rather she didn’t do it. “I want to be changed,” he replied noncommittally.
Cindy leaned forward again and said a bit softer. “So then you want me to change you?” she asked hopefully.
Chad didn’t know why she wanted to drag this out. As far as he could see, the fact that she would be changing him instead of Cassie was probably a foregone conclusion. If she was going to do it, then he’d just as soon get it over with. “Yes,” he replied somewhat testily.
“Tell me again,” Cindy said with a bit of a giggle. “Tell me you want me to change you.”
Ugh! “I’d like you to change me,” Chad replied. Then, to end the pointless banter between them, he added the word, “Please!” Hoping it would get her moving.
Excitedly and almost defiantly, Cindy held her head high and said, “Then let’s go,” as she came out from behind the tall desk and led the way toward the back of the gym.
They met Cassie heading towards them about halfway through the big room. “There you are,” Cassie said. “I was beginning to think you were late today. Thanks Cindy. I’ll take him from here.”
“But he asked ‘me’ to change him today.” Cindy replied a bit defiantly.
“No!” Cassie replied sternly. “I told you earlier… No!”
“But!”
“No! And don’t ask again! Now get back up front where you belong!”
Defeated, Cindy headed back to her station at the front counter.
Chad was grateful, but he realized that he had obviously missed something. Maybe Cassie didn’t want Cindy changing him because of the way she had banged on his chastity device the last time with those scissors. Either way, he was glad that Cassie would be doing it!
“So, did you really want Cindy to change you instead today?” Cassie asked a few minutes later as she started pulling things out of his diaper bag.
“Heavens no!” Chad replied. “It’s just that she can be so…” he searched for the right word.
“Manipulative?” Cassie suggested.
“Yeah. Manipulative!”
“So you’d rather have me doing this than her?”
“I’d much rather you do it!” Chad replied with conviction.
Cassie reached into her desk drawer and pulled out the toy she used on his backside every day. “I wonder why?” she replied jokingly.
A short while later, she was holding firmly onto that toy as Chad pumped his back end against it furiously. Once again she was struck by how desperate he seemed to be. And once again, she noted how defeated he was when he gave up. But that didn’t seem to keep him from trying every day. She actually felt for him. She just wouldn’t let him know that. Just as she didn’t let him know that she was only faking putting the suppositories up inside of him – from now on.