The Bet - Chapter 58 (Sunday – week 9 Part 3 of 7)

The Bet

By Karen Singer

Chapter 58 (Sunday – week 9 Part 3 of 7)

     She was gone for a while, but he hardly noticed.  His mind was simply at peace as he waited for her.  And when she returned, he looked up from his kneeling position, but that’s all he could do. 

      “Lay down there, Sissy,” she told him. 

     He laid down on the middle of her bathroom floor.  A moment later, he felt the nipple of a baby bottle pressed to his lips.  His lips parted to take the bottle even as his hands came up to hold it.  The tea in the bottle was still warm, but not too hot.  He was grateful for the bottle.  He hadn’t realized before that he was even thirsty, but he was now that he had something to drink. 

     He expected her to remove his blindfold then, but she didn’t.  Still deprived of his sight, he felt her moving around him, then straddling his body.  The cold firm pressure of the first breast form being pressed to his chest was his first clue as to what was going on.  Oh well, it had been nice to go so long without them.  A real treat.  But obviously that was over now.  Shortly after that, he was getting used to the weight of both breasts once again firmly attached to his chest.  It took a little bit to get used to them again, even just lying there on his back drinking his bottle.

     Again he expected her to remove the blindfold, but she didn’t.  And soon he felt her removing his wet diaper.  Not leaking – he didn’t think, but just very wet.  Very quickly, he was in a fresh dry one – which he knew wasn’t going to stay dry for very long – if it wasn’t wet already. 

     And once again he expected her to remove his blindfold… and once again she didn’t.  Instead, she started talking to him.

      “I was going to tell you this yesterday,” she said, “but somehow, my plans got changed.  I’m making a new rule for your diaper leaking requirements.  You still get an hour and forty-five minutes to get it leaking, that much hasn’t changed at all – and it won’t!  I’m not going to lessen that amount of time for you at all, especially since by all indications, you’re doing very well at always getting your diapers to leak on time.  I’m still not going to punish you unless it takes longer than that.”

     Chad was grateful to hear that part.  An hour and forty-five minutes could come all too quickly!  And some diapers were just plain stubborn when it came to leaking!  It was what she hadn’t said yet that had him worried.

      “But I’ve noticed that you very often manage to be leaking in closer to an hour and a half.  Sometimes less.  So for that reason I’m going to offer you a little reward – of sorts.  From now on… which I guess will be until Friday comes, for every minute less than an hour and a half that you manage to get your diaper leaking, I’m going to let you play with one of my toys in your backside to get what pleasure you can.  And I know you like that!  You can play with it right then when you change your diaper… or, if you like, you can save up those minutes to use at the end of the day so you can play longer.  But if you don’t use that time every day, you lose it.  It starts all over again every morning.”

     Without his eyes, there was no way that Chad couldn’t concentrate on everything she had just said.  And she was right, he really did like having his bottom played with.  And now that he wouldn’t be going to the gym anymore where Cassie had done it, the chance to play like that sounded twice as good.  But the question was, could he make his diapers leak in that amount of time?  At least she wasn’t lessening his time limit.  He didn’t think he could manage that if she did.  But an hour and a half?  It was the old carrot and stick approach… with a fifteen minute interval in-between.  More than an hour and forty-five minutes and he got punished.  Less than an hour and a half and he got rewarded.  But somehow he wasn’t all that sure about how successful he was going to be gaining that little bit of time as a reward.  So was it worth it?  He really wasn’t sure.  He would have to see.  At least he still had his hour and forty-five minutes to work with!

     Mel reached out and pulled the blindfold off his head.  With the bottle still pressed to his lips, Chad blinked several times as his eyes got used to being able to see again. 

      “You can lay there till you finish that thing,” she told him.  Then get dressed.  We have grocery shopping to do today.” 

     The grocery store still held a lot of fear for him, but not like it used to… and especially not today since he was once again attired in his maid’s uniform instead of some of the other outlandish garments she had made him wear.  A maid’s uniform… which would call all too much attention to him, yet at the same time, compared to other outfits, he almost felt properly dressed.  He revised that thought.  He was properly dressed – for a maid… which he guessed he was… for now.

     As they left the car and walked into the store, he couldn’t help remembering that time early on in the bet when she had actually called the police before he relented and got out of her car to follow her into the store – wearing a skirt.  Now… well… skirts and dresses were the only thing he ever wore – anywhere.  It was amazing how used to it he had become in such a short time.  And yet… there was still that same fear rooted somewhere deep inside of him.  It just wasn’t as worrisome now as it used to be.

     As usual, he grabbed a cart and set his purse and diaper bag in the child seat before following Mel up and down each of the aisles.  As far as he could tell, they didn’t really need much.  Most of their cupboards were fairly full, as was her refrigerator, although that was mostly full of baby bottles now. 

     As they usually did, he grabbed a few things and threw them into the cart, and Mel did the same.  But when they got to the aisle where the tea bags were, Mel stopped and just stared at the boxes of green tea.  Did they need any?  They still had some at home, just not a lot.  But really, there were what, about five more days until his testing started?  And after that the green tea wouldn’t be needed anymore.  Should she buy some?  Or not?  She glanced a few times back and forth between the boxes of tea and Sissy.  Then deciding to just make sure they would have enough, she grabbed one box only and threw it into the cart. 

      “Not much time left anymore,” she said to Sissy.

     Despite being out in the grocery store, Chad curtseyed.  “No Mistress.  If you count today, that’s only five more days before Friday.”  Curtsey.  He saw her nod and move on.  Five more days of living the dream.  Not much. Not much.

     They were in the middle of the store when Mel reached into her purse and pulled out one of the recently filled baby bottles and handed it to him.  Chad had really hoped she wouldn’t do that.  But having done it before, he put the bottle to his lips as he pushed the cart.  And a few aisles later, they reached the baby food… where Mel stopped… and looked back at him… and smiled all too wickedly.  Chad’s brain did a bit of a mental flip as he remembered that she had told him he would eat nothing but baby food until their bet was over with.  Even out in the restaurants!  That thought alone sent a tiny spark of sexual thrill through him.  Talk about embarrassing!  Almost as embarrassing as walking around in the grocery store in a maid’s dress sucking on a baby bottle.  As if nobody would possibly notice!

     Mel didn’t waste as much time as she usually did looking over what was available before putting it in the cart.  She just started grabbing jars from everywhere.  One thing Chad became quickly sure of, he wasn’t going to run out of baby food anytime soon.  But looking at the baby food also reminded him that he hadn’t eaten anything yet today.  His stomach growled a little in agreement.  He took it as a bad sign that the sight of baby food should make him hungry!

     As they left the baby food aisle, their cart was noticeably loaded with baby food… and he was still drinking from his baby bottle – while his maid’s dress called all too much attention to him.  The looks he got from all too many of the customers kept his face very red with embarrassment.

     They were halfway down the next aisle when Mel’s phone started ringing.  She quickly fished it out of her purse.  “Hello?”

      “Where are you?”

      “Derek?”

      “Of course!  Who else?”

      “I don’t know.  We’re grocery shopping.”

      “Oh,” Derek replied somewhat surprised.  “I didn’t think of that.  It’s something I don’t do much myself anymore.”

      “In other words, you eat out all the time.”

      “Wouldn’t you?”

      “Not that often!”

      “So when will you be home?”

      “We’re almost done.  Are you thinking of coming over?”

      “I’m already there!”

     Mel paused for a moment.  “Okay, we’ll try to hurry up.  Give us about fifteen minutes.”  She hung up her phone.  “We need to get a move on, Sissy.  Derek is already home and waiting for us.  And that bottle better be finished before we get out of here!”

     As Mel drove home, she was a little put off that Derek had shown up uninvited again.  Actually, it wasn’t that he had shown up like that, she kind of considered it sweet.  It showed that he liked her.  It was just his assumption that she would be there waiting for him and would have nothing better to do.  At least he could have been polite enough to phone first!  Not that it was really a problem.

     She couldn’t help but notice Derek’s big SUV as she pulled into her parking space.  And as she and Sissy got out of her car, he got out of his. 

     Derek paused as he walked over to her car.  He paused because the sight of Sissy in his maid’s dress momentarily stopped him.  But a moment later he continued on and gave Mel a small kiss on the cheek to greet her.  “Want some help with that stuff?” he asked.

     Mel shook her head.  “No, Sissy can get it.”  She led the way up to her apartment, leaving Sissy to get all the bags.

      “So, is your ballet thing over with now?” Derek asked as soon as they got up to her apartment.

      “You… should have been there!” Mel replied with a grin.  “It was hysterical!”

     Derek couldn’t imagine anything about ballet being hysterical – even if it was Sissy who was performing it.  “Uh…  Let’s just say that dancing, of any sort, is not my thing.”

      “Pity!” Mel replied.  “Just what is your thing, by the way?”

     Derek shrugged.  “Work.  What else is there?”

     Mel realized that it was the one thing she already knew about him.  He spent most of his time working and did little else.  It was the reason he was now divorced.  “You need to find some other interests in life.  Things that make you happy.”

     Derek smiled.  “You make me happy!”

     Mel smiled.  “Flattery will get you everywhere!”

     Sissy lugged armload after armload of plastic grocery bags up the steps and into her apartment.  At least she wasn’t making him carry them one at a time today.  In fact, since Mel and Derek were just sitting in the living room talking, he wasn’t sure if either of them knew he was even there.  As soon as he got everything inside, he automatically grabbed another baby bottle and started putting everything away.  As he drank from his bottle he checked the time.  What worried him was that he didn’t think his diaper was as wet as it should be with the amount of time he had left to be leaking.  But then, he hadn’t really had nearly as much to drink today as he usually did.  He took a moment to just drink from his bottle before continuing to clean up the kitchen.

     The other good thing about drinking from his bottle, was that it helped with his feeling of hunger.  After grocery shopping and now putting all the food away, he was definitely feeling the lack of breakfast.  He briefly wondered if he could eat something while they were talking.  Since he was being totally ignored, he finally decided to do just that.  After all, wasn’t it proper for a maid to not bother her Mistress with trifling details? 

      “Oh, by the way,” Derek said as they reached a small lull in their conversation.  He reached into his pocket and fished around for a moment before withdrawing his hand again.  He opened it to display what he had found.  Two bent and misshaped cup hooks and a pair of screw-on earrings with some thin silver chain dangling down.  They didn’t look expensive at all.  In fact, they looked rather cheap and… ugly.  “Remember my little idea for keeping Sissy in place on that stand you’ve got in the corner for him?”

      “His perch?” Mel asked. 

      “You said I could try it if I wanted.”

     Mel remembered.  It was the time that Sissy had been there so long he had actually fallen asleep right there on his perch, and his head had turned to the side in the process.  She really wasn’t too sure about wanting to use Derek’s idea, but she decided it couldn’t hurt to let him go ahead and try it.  Besides, since he knew about Sissy and wasn’t being all that accepting of him, maybe it would be better to let him have his little bit of fun and try his idea.  But still…  A bit hesitantly, she asked, “Are you sure it won’t hurt him?”

     Derek shook his head.  “No.  See here, I found these screw on things instead of the pierced ones you usually wear.  That way with enough effort, they can always slip off of his ears.  Besides, with these it won’t matter what earrings he’s already wearing.  He doesn’t even have to remove them.  Just screw these in place and hook the chains over the cup hooks attached to the wall, and if I’ve figured this out right, he’s not going to be able to turn his head much at all.  And I doubt he’ll be going anywhere if you just do something to keep his hands off of them.”

      “Like tying them behind his back.”

      “Well… yeah.”

     Mel nodded, then shrugged.  “Try it,” she said, giving him permission.  “I’ll go get him.”

     Sissy had looked longingly at the food in the refrigerator as well as the food that Mel had in her cupboards… the ones that didn’t hold baby food.  Did he dare eat something that he knew she didn’t want him to? 

      “What are you doing?” Mel asked as she walked into the kitchen.

     Horrified that he had been caught, he curtseyed.  “I’m hungry,” he replied.  “I was just thinking about eating something so I wouldn’t have to disturb you.”

     Mel stopped before she could say anything else.  “Oh my God!  I totally forgot that you hadn’t eaten!”  With a normal servant she wouldn’t have cared as much.  But this was Sissy, and for now he was her total responsibility.  Besides, if she didn’t keep putting liquids and food into his system, there wouldn’t be enough to keep coming out to cause his incontinence.  And… she simply felt bad about it.  She turned back toward the living room.  “Derek, you’re going to have to wait a little while on that.  I’ve got to feed Sissy first!”

      “What?  Why?” Derek asked as he got up from his seat and headed for the kitchen.

      “I haven’t fed him at all today.  He’s hungry!  And he’s my responsibility!”

     Derek wasn’t at all sure about her logic, but he did know that she felt strongly about it – for whatever reason.  “Okay,” he replied.  “Do what you have to.  This was just an idea I had.  It can wait.”

     Mel didn’t care if he could wait or not.  She quickly opened the cupboard where all his baby food was stashed and started pulling jar after jar out.  As she did, she again noticed that his highchair was missing.  “Sissy, go get your highchair, right now.  We need it!”

     Chad was a bit embarrassed by that – in light of the fact that Derek was there, but he turned and headed for the door.  He went out and walked down to Sandy and Cassie’s apartment.  Where he knocked, hoping that nobody was home.  Unfortunately, Cassie answered the door fairly quickly.  He curtseyed.  “I need the highchair,” he told her in his sissy voice before curtseying again.

     Cassie stood back to let him in.  Chad started to step over the threshold, but he stopped himself quickly.  Curtsey.  “Um… If I go in, then I have to crawl,” he told her before curtseying again.

      “Just go get it,” Cassie replied with a bit of annoyance.  “And don’t worry about it.”

     Chad hurried inside.  He found the highchair in the kitchen and started to pick it up.

      “Who is it?” Sandy asked as she came out of their bedroom.

      “Sissy’s just getting the highchair,” Cassie told her.  “I told him he could walk this time.”  She had said it in such a way that Sandy knew better than to protest. 

     Chad lugged the heavy chair outside as Cassie held the door open for him.  He set the chair down and curtseyed.  “Thanks,” he said sincerely.

      “No problem,” Cassie replied with a hint of a smile.

     Chad picked up the heavy chair and lugged it back toward Mel’s apartment.  As he got close, he saw Derek stick his head out looking for him.  “Geez!” Derek said.  “You look like you’re going to hurt yourself with that thing!”  He walked all the way out of the apartment and met Sissy part of the way back.  “I’ll carry it for you.  You make it look like it weights a ton!” 

     Chad gratefully set the chair down and stood back for Derek to grab it.  He had no illusions about how much stronger Derek was than him.

      “I’ve seen women who are stronger!” Derek muttered as he easily picked the thing up and carried it into Mel’s apartment.

     It was embarrassing, but what could he do?  He simply wasn’t the big strong muscular type!  As he got back to the kitchen, he saw Derek placing the chair right where it was supposed to be.  He also noticed how much baby food Mel had placed out on the counter.  More than usual.  He had a bad vision of the day before when she had made him eat so much he nearly got sick.

     There was no doubt about it.  Being placed into his highchair, having the tray stuck in place, and having a bib tied around his neck – all in front of Derek was embarrassing.  Even though he was wearing his maid’s dress.  Having a plate full of nothing but baby food mush being set in front of him with only a tiny baby spoon to eat it with was also embarrassing.  The two baby bottles Mel set on his tray as well didn’t help matters either.  He was glad to see though, that while she had given him more food than usual, it wasn’t nearly as much as she had tried to make him eat yesterday. 

      “Since it’s almost lunchtime,” Mel told him, “I’ve given you more than usual.  And two bottles because you’re time’s running out!  And since Derek is here, if he wants to do the honors to punish you, then I’m going to let him.  So I suggest you drink up!”

     Chad glanced around at the clock.  She was right!  He didn’t have much time left.  He grabbed one of the bottles quickly and started drinking, ignoring the rest of his lunch set in front of him.  Leak!  Leak!  He had made a big mistake today in not drinking as many bottles as he needed to.  And now he was worried about paying for that mistake.  Leak!  Leak!

     Mel laced her arm through Derek’s.  “Let’s go back and sit again.  I’m afraid he’s going to be a while.”  She turned her head back toward Sissy.  “Unless he calls to tell me he’s leaking… which he better!”  She led Derek right back to the living room again, leaving Sissy alone with his lunch and his bottles.

     Chad drank furiously.  As hungry as he was, he was far more worried about being punished than easing a little bit of hunger.  Especially since it would be Derek who would be punishing him.  Leak!  Leak!  More and more often he turned his head to look at the clock.  He knew he was extremely wet, but was he wet enough to start leaking?  That, he wasn’t too sure of at all.