The Bet - Chapter 31 (Monday – week 5 Part 8 of 8)

The Bet
by Karen Singer

Chapter 31 (Monday – week 5 Part 8 of 8)

As Mel drove towards home, she kept glancing in her rear view mirror at him. He was still crying softly, feeling sorry for himself. She felt bad about that – in a way, but mostly, she felt like she had succeeded. There was no elation, just that sense of having gotten the job done.
She didn’t say a word as she drove home. When they got there, they both helped to carry all the bags up the stairs to her apartment. She was relieved to get there. She had taken a big chance with what she had just done, but she had gotten away with it… she hoped.
She turned to Sissy who was just starting to pull empty baby bottles out of one of the bags. “Go change into your uniform, Sissy. It’s time to get back to other things.”
Chad was grateful to get back into his maid’s dress. It made him feel a bit more grown up again. But the fact remained that he was still a big sissy. Having Mel remind him that he was working on yet another two hour time period to get his diaper leaking again didn’t help matters either.
Back in his own apartment, it took him only a few minutes to remove the sissy dress he had been wearing, slip into one of his maid’s dresses, slip the comfortable shoes on, and tie an apron neatly around his waist. He stared at his reflection in the mirror that was attached to his closet door. He dropped a little curtsey to himself. Sissy!
He fixed Mel a nice dinner that night, trying something new from his cookbook again. Dinner was mostly a success, he figured. She didn’t say anything. In fact, since they had gotten home, she had said very little. But that was just as well, he didn’t really feel much like talking, especially if he had to use the silly sissy voice that she was requiring. His dinner was yet more baby food, eaten from his highchair. How exciting.
Mel sat in one of her living room chairs while Sissy did the dishes. She had watched a show on TV, but had barely paid attention to it. She turned the set off. There was a slight air of somberness in the apartment. She could almost feel Sissy’s mood. Well, he had to be taught a lesson. But the question now was, did he learn the lesson she hoped he did? It was going to be hard to tell. Maybe the future would hold the answers. Maybe not.
She heard the water go off at the sink, then she watched as he wiped the counters down and put away the dish towel he had been using. He glanced around the kitchen and seemed satisfied. She followed his movements as he left the kitchen and started looking around. He straightened up some magazines, then checked the laundry. Both machines were off. He was looking for something to do. “Sissy,” she called. He came over to her. She could see the depression still on his face. Obviously, he had learned some kind of a lesson today.
He curtseyed. “Yes, Mistress?”
She smiled at his curtsey and greeting. Yes, this was living. This was what she loved. And dinner hadn’t been half bad either. She really loved seeing him in his maid’s uniform… totally subservient to her every whim. She didn’t understand how everyone else could be so bored by it. Yet she did understand the thrill they got from seeing him in his other sissy clothes.
“You wanted something?” he asked, since she didn’t answer.
She didn’t know what she wanted. She just wanted him near, where she could see him. “Is your diaper leaking yet?” she finally asked.
“No, Mistress, not yet. But I still have plenty of time,” he added quickly.
She nodded. “I know. Just let me know when it starts leaking.” She realized something then. Other than the bottle she had seen him drink with his dinner, she hadn’t seen him with any other bottles since they had gotten home. “Are you going to make it?” she asked.
This time, he nodded. “I’m fairly sure I will,” he replied.
“I haven’t seen you drinking much.”
He shrugged his shoulders. “I don’t think it matters anymore. I’m still wetting a little every few minutes.”
She nodded. “Let me know.”
He curtseyed again as he acknowledged that he would. His curtsey thrilled her again. It always did. There was just something about seeing a man do that… a man dressed like a woman… a subservient woman. All his male traits taken away, denied him. Submissive to her. Courteous to her. Attentive to her… and to her pleasure.
She watched as he started walking around her apartment again, looking for things that needed to be done, where nothing really needed attending to. She was tempted to have him stand on his perch again, but the words to order him to do so never left her mouth. He wandered and touched this, and did… nothing really. She could see that he did have something on his mind still. The lessons from earlier?
His dress was neat as a pin. The large white bow she had tied in his hair earlier was still there. She decided she liked the look with his uniform. With the breast forms glued to his chest, his shape was definitely more feminine than masculine – another male trait taken away. The only real indication that he was still male was in his shoulders, which really weren’t all that bad at all. His face too held a certain bit of masculinity, despite the makeup that covered it. She stared at his face as he walked around the room. It was a nice face. She knew it could show kindness… or love. His eyes alone could express so much. She adored the way he often looked at her with them. His lips, even covered in the bright lipstick, looked inviting, kissable. Overall, he was a very pleasing sight. Very.
She saw him suddenly jolt with surprise. He looked quickly down, then back up at her. He hurried over to stand in front of her. He curtseyed and she felt it stir those lovely sensations deep inside of her, sensations that were quickly starting to lead to other lovely sensations.
“I’m leaking,” he said quickly as he turned his leg sideways to see if any had dripped down below the hem of his skirt far enough that she could see it yet.
She didn’t really care anymore. She didn’t care if he had done it before his deadline was up or an hour later. The sight of him in his uniform had her ready to move on for the evening. She looked up into his beautiful sissy face. “Then let’s get you changed.”
Chad expected her to change him right there in the living room again, or perhaps in her bathroom, but she led the way instead to her bedroom. He was surprised to see her laying out protection on her bed so it wouldn’t get ruined in case he wet some more, which was now all too likely. She glanced at him. Did she want him to do something? But then she started adding yet more layers of protection to her bed. He realized then that she had something else in mind entirely. It took him only a moment to realize what that something else might be.
“Get that dress off, Sissy,” she ordered as she worked on her bed.
Finally stripped down to just his single leaking diaper – and his breast forms – she pulled his soggy diaper off of him before she had him lie down on her bed. Within moments, she had him rediapered in nothing but a single diaper again. He waited for her to tell him that he was on another two hour time limit, but she never mentioned it. Instead, she went over to her dresser and pulled out one of the scarves that she used to blindfold him with. A minute later, Chad could no longer see anything.
He heard her moving around, doing something. Probably undressing. She climbed up on the bed with him. He felt her lying down next to him, her naked body hugged his for a moment, then she backed away again. Blind and without direction, he didn’t know what to do. He felt her hand on the front of his diaper. She was pressing down… down on his chastity device underneath. She pressed it firmly into his groin, then suddenly the pressure and her hand was gone again. Her hand came back to the same place, her touch more gentle now, probing. What was she doing? She had to know he couldn’t get hard there – not with that chastity device in place – that is, if he could get hard there anymore.
Mel removed her hand. She didn’t even know why she had bothered to touch him there. Curiosity perhaps? Wishful thinking perhaps? But all she had felt inside his diaper was the hard plastic of the chastity device. And of course it felt exactly the same after she had pressed on it. He was denied that pleasure, but the thought of him being denied sent more tingles of pleasure through her.
She wanted to touch him. To feel him. She climbed on top of him, straddling his stomach. She ran her hands down the sides of his face, down his neck, down between his breasts, then rubbed them slightly on his stomach. Smooth and hairless. Beautiful. Did he feel anything from her touch? He couldn’t react where she knew he wanted to react, but how about anything else? She really hoped so. For his sake, she really did.
She rolled off of him, next to his naked form, and pulled on his body. “Hold me,” she whispered. “Make love to me.”
Two commands that Chad only dreamed he’d ever hear. He was once again denied his sight, but he could still feel her. He rolled over and climbed on top of her, just as she had been on top of him. He was denied any of the pleasure that might lead to sexual relief, but that didn’t stop any of the pleasure he could get from caressing her naked body – even if he couldn’t see it. He could feel her body, massage it, love it. And he did.
Mel writhed under his touch. Magic. And when he started massaging her breasts her breathing became deeper, almost panting as the pleasure and ecstasy mounted inside of her. She knew he couldn’t see her, but those magic hands of his certainly had no trouble making her feel good – all over. His hands went from massaging both her breasts to just her right breast. He squeezed it gently, massaged it. Then, he started leaning down toward it. She held her breath. She could feel his breath now against her nipple as he leaned down ever closer. Ever so gently, his lips reached out and kissed the nipple. She moaned aloud in pleasure. And when his tongue reached out and flicked that same nipple, she involuntarily arched her whole back, writhing beneath him from the wonderful sensation.
She wanted him. She wanted him badly. She wanted to feel him inside of her, filling her completely. But she had denied him that ability. Yet she still needed him. Needed his attentions. She pushed down on his shoulders, pushing him backwards, further and further till he was between her legs. Her waiting sex pushed upwards towards him over and over again. She grabbed his hair and pulled his head down, first gently, then harder. She was becoming more desperate now, she quickly got his head in the exact spot where she needed it and was instantly rewarded by the feel of his tongue flicking out and touching the very spot that craved it most. She wanted to scream with pleasure. Her legs closed around his head, trying to feel more of him in that region. His tongue came again, then again. Faster and faster. Then deeper and slower. Then deeper still. Licking, massaging, caressing, exciting. His hands squeezed against the sides of her butt. His tongue licked particularly hard, and she lost all sense as her body rocked beneath the orgasm that had been building for some time now.
Chad heard her moan, he heard her scream. He felt her body reacting to his touch in so many ways. He was glad he could afford her this pleasure. It made him feel good, like he was still worth something. And then there was the pleasure he received from just touching her naked body… her full round breasts, her smooth naked skin, her wet waiting sex. Touching her like this was something to always be remembered.
With his head pulled into her groin, he couldn’t lift it away, not that he wanted to. He could feel how much pleasure she was receiving from his tongue. He let his hands start wandering her body, caressing it wherever he could reach. He felt her mounting again toward another orgasm. This one seemed to last even longer than the last one. When it was done, he kept at it, kept teasing her with his tongue, but she didn’t keep him there but only a minute.
Mel felt wonderful. Her breathing was slowly calming down, and his little flicks of his tongue were again driving her wild. But she was ready for something else. Pulling gently on his hair that she had locked in her two hands, she pulled him up, further, further, till he was climbing on top of her. She guided his body till it was once again laying next to her. “Hold me,” she whispered. And he did. His gentle hands occasionally reached out to caress one part of her body or another. She did the same to him, occasionally gliding her hands over his body. Over and over again, she gently rubbed them over the breast forms glued to his chest. She toyed briefly with the fake nipples on each of the forms. Did he feel anything at all from her caressing there? She silently hoped that he did. Men had no idea what pleasures they were missing by not having breasts. But he wasn’t a man… well, he was… but he wasn’t. Not really.
She finally moved away from him, rolling off of the bed. “Stay,” she commanded softly. “I’ll be right back.” She watched till she saw him lay back, getting comfortable, ready to wait for her.
She left him and quickly went into her bathroom where she cleaned herself up and dried herself off. Then she donned her nightgown. Finally, she went back into her bedroom. He was still lying there, just as she had left him. “Don’t move,” she said softly. He only turned his head.
She found the package that held the collection of colorful dildos that had arrived in the mail. She opened it, and stared at the collection. Each one was in a different sherbet color. Each one had its own unique shape. There was one with a spiral corkscrew shape that seemed to catch her attention more than the others. She almost selected it, but then decided that maybe she would save that one for herself. She was tempted to grab the one that was ribbed like the one that Cassie had said that he seemed to like so much, but she didn’t. Instead, she grabbed the one with little tiny knobby bumps all over it. It too looked awfully interesting to her. Maybe someday. But today, she would see if he liked it.
She carried it to her bathroom where she tried to wash it off quickly, but there didn’t seem to be much of a point since it was already clean. She dried it off again. Time to play.
Chad heard her finally coming back. She had been gone for quite a while, well, away from her bed anyway. Could he take the blindfold off yet? He didn’t dare touch it or even ask. He was surprised to feel her removing the diaper she had just put on him such a short time ago. It was already wet – multiple times.
He felt her hands touching his chastity device, moving it slightly this way and that. Would she remove it? He hoped fervently that she would. But so far, she was leaving it in place. What was she doing?
Mel stared hard at his tiny penis, trapped inside of the hard plastic. She had tried playing with the device as best as she could, but as far as she could see, there was no reaction from him on the inside. None at all. Maybe something else would stir his interest. “Roll over,” she commanded gently.
Roll over? Chad was disappointed that she wasn’t going to remove the device. But he did as she told him and rolled over onto his stomach. He felt her caressing his backside for the briefest of moments, then he felt her wiping it with what felt like one of his diapers. Her hands came back. They lingered longer this time, then left again. He heard her doing something. He jumped as something cold hit his naked butt. Lotion. Then her hands were back again, rubbing it in, massaging it in. He nearly sighed out loud with pleasure as he let his body relax into the feeling. So nice.
Her head came down near his. “Pull your legs up,” she told him. He knew what was coming next… at least he hoped he did. It was definitely something that he wanted. He pulled his knees up under him, raising his backside up for whatever attentions he hoped she would give to it. He jumped as more coldness suddenly hit him, right on top of his anal hole. Then her finger was there, gently pushing, then firmer. He relaxed and with a wave of pleasure, allowed her finger to slide into him, spreading the lubrication all around. So wonderful. He hated feeling her finger leave him. But her finger was soon replaced by something harder. Something larger.
He felt her pushing firmly almost immediately. Not quickly, but firmly. Slowly she pushed it in. He nearly jumped when he felt the first little bump go past. What was she using on him? The first bump was quickly replaced by another one – in a different place. What the…? Then more, many more, all over. She continued to shove it in slowly, then she backed it out just as slow. He was constantly assaulted by the little bumps going in and out. Each one seeming to add so much to what he could feel, thereby increasing the pleasure he felt. Whatever she was using was different, but that’s the limit of what he was capable of thinking as she began pushing it in and out faster.
Within moments, he was pushing back and forth himself, trying to get even more out of the device than what he was capable of feeling. He wanted more. Much more.
Mel watched him reacting to her new toy. He seemed to like it. In a way, he was being used like a woman would be used by a man. Her thoughts turned again to the strap-on. Would he like it? It was without a doubt a bit bigger than what she was using on him now. But then he seemed to be taking that with no problem. But would he like it? Being fucked by her as if he was a woman? She considered trying it… strongly. But there was something about the act of doing it that she herself wasn’t quite ready for yet.
He was tiring, she could see it plainly. As he slowed, she slowed. She saw his fist pound against the mattress in frustration. No release. She felt sorry for him in a way, but she still wasn’t ready to release his penis from its prison. His denied ability to use that masculine appendage still meant too much to her. He stopped rocking completely. She stopped too. Then slowly she withdrew the toy. He didn’t move, he only continued to breath heavily, trying to catch his breath. “Roll over again,” she directed.
Chad heard her, but it was a moment before he found the will to do so. Slowly he rolled over onto his side, then onto his back. Still blindfolded, he felt her playing with his chastity device again. Would she take it off now? Now that they were finished?
Mel again looked hard at his tiny penis inside the chastity device. As far as she could see, it was still no bigger at all. She knew he had gained pleasure from her toy, but none of that pleasure had translated into a reaction from his primary pleasure point. Interesting!
He suddenly started peeing again and she quickly pulled one of the diapers over it to keep it from spreading. Did he even know he was going to pee? She could only hope not! “Stay here. I’ll be back in a few minutes,” she said.
Chad felt more then heard her leaving him. He was tired and frustrated… and glad for the break to just lay there and relax. Her bed felt good, far better than his little blow-up mattress. When she came back, she told him to raise his bottom up. He felt her sliding fresh diapers under him. A minute later, he felt her finger invading his backside yet again. The darn suppositories. He hated them. Why couldn’t she just forget them for once?
Mel pulled her finger out of him. She saw the look of displeasure on his face at having to have another of the suppositories. She smiled. What he didn’t know though, was that tonight marked the start of another piece of her master plan. Tonight was the first time he would be going to bed without one stuck up inside of him. She just needed him to think that it was there. Would he still mess himself like he usually did every night? She was fairly sure that he would. One at a time, she brought the disposable diapers up and pinned them in place. All four of them. Then she pulled the plastic panties onto him that she had grabbed from his diaper bag and pulled them up into place as well. He was now well padded. “Sit up,” she told him. When he was sitting, she finally removed his blindfold.
Chad blinked, then rubbed his eyes as soon as the scarf was removed from his head. He looked at Mel. She was dressed again – darn it! But then he had really expected that. “Stay here,” she told him. “I’ll be right back.” He watched her as she left the room yet again. He briefly wondered what she had in mind for him now. But he was mostly too spent to worry about it very much. He sat there on the edge of her bed and waited. She wasn’t too long. She came back with three baby bottles cradled in her arms.
“Sit up on the bed,” she told him.
He climbed back up on the bed and was surprised when she climbed up next to him. She set all three bottles on her nightstand, then sat up against the headboard. She stared at him for a moment, considering how she wanted to do this. “Lay down,” she said, then she patted her chest just above her breasts, “with your head right here.”
Chad wondered if she was planning on feeding him the bottles herself? That would be odd. Why? But he did as he was told and laid back with his head on her breast. He could at least dream of other, more pleasant, things. Of course, this was certainly pleasant. Very pleasant.
Mel grabbed one of the bottles and stuck it down into his waiting lips. She giggled a tiny bit as she did so. He took the bottle just like a baby. He was her baby. His eyes closed as he drank. She watched him nursing on the bottle for a very long time. When the bottle was finished, she replaced it with a fresh one. Gloria had been wrong. She had been wrong when she said that he wasn’t a baby that she could hold… or feed. Okay, so he wasn’t a real baby. But in all other ways, he was certainly close enough. Was this little action bringing out some of her maternal instincts? No, she didn’t think so… well, maybe some. But mostly no.
He was her baby in so many ways. Yet he wasn’t her baby at all… he wasn’t a baby at all. Which to her made the situation all the better. No, Gloria was definitely wrong about their relationship. It was just a fun relationship. Hopefully for him as much as it was for her. That was all she really needed it to be. Nothing more. But certainly nothing less.
When his second bottle was finished, she replaced it with the third one. He was drinking slower now, much slower. She yawned. She was tired, and sexually sated. Very sated. She felt wonderful. And holding him in her arms like that was nice. Very nice. His bottle was almost done. She was so tired. She pulled it out and set it on the nightstand. Still holding him, she scooted further down in the bed where she could be more comfortable. He didn’t move. Was he asleep? She needed to wake him and send him home, but she just didn’t feel like it yet. She’d do it in a few minutes. But one minute later, she was dozing herself.
Half asleep, she was too tired to get up. She was also tired of holding him. She shoved at him a bit to wake him. “Hold me,” she said. “It’s my turn.”
He woke out of his light slumber, surprised to still be there in her arms, surprised at her words. He shifted up higher in her bed and put his arm out. She laid her head on his shoulder and curled her body up into his. He couldn’t believe it. He was laying here in her bed, holding her while she slept. How did that happen? One thing he knew for sure though, he wasn’t about to do anything that might wake her. This was an experience to be remembered. This was an experience to be savored. He would hold her like this all night if he had too, and he would do it gladly.
Very slowly, he stretched his head down and lightly kissed the top of her hair. “Good night, Mistress,” he whispered softly. “Good night.”