The Bet - Chapter 54 (Wednesday – week 8 Part 5 of 9)

The Bet

By Karen Singer

Chapter 54 (Wednesday – week 8 Part 5 of 9)

      “Champaign!” Mel squealed in delight as Gloria told how Ray had shown up at her office door last night.  “It’s positively romantic!”

      “It was romantic alright,” Gloria agreed.  “In more ways than one.  Do you know I think he prides himself on his bag of sexual tricks?”

      “I believe it!” Mel replied.  “I remember how he went through one after another with me.  Is that how he was on your first date?”

     Gloria shook her head and blushed a bit.  “I don’t think I ever gave him the chance.  I was too busy trying to go through all my own fantasies.  Which I have a lot of by the way.”

     Mel laughed.  “Well, we each went through some fantasies last night then,” she replied.

     Gloria became a bit more serious.  “Yeah, how’s that going by the way?  How does the relationship between you and Derek and Sissy seem to be?”

     Her question made Mel become a bit more serious too.  “It’s… going,” she finally replied.  “He seems to resent Sissy’s presence an awful lot.”

      “Can you blame him?”

      “Not really.  But I’ve been totally up front with him about it.  For now, I’ve got to keep Sissy on a really tight leash until this bet is finished.  The end is too close for me to let up in any way at all now.”

      “And naturally, Derek would rather be alone with you instead of having Sissy around all the time.”

     Mel nodded.  “Exactly.”

      “And how is Derek relating to Sissy… now that he knows all about him?”

     That question clouded Mel’s face even more.  “Awkward wouldn’t even come close.  As I said, he resents Sissy terribly.  He mentioned several times how he feels like Sissy… or Chad rather… betrayed him.  They used to be friends, and now… well, now that he knows the truth about Sissy, he can’t seem to feel anything except revulsion for him.  I know that eventually he’ll probably mellow out – at least a bit.  But for now, well, he still seems to hold a lot of anger toward him. 

      “So does Derek try to avoid Sissy?”

      “No, not really.  But while he’d rather Sissy wasn’t there, he says he’s determined to not let Sissy get in his way.  But I noticed that Derek doesn’t seem to mind taking his frustrations out on him.  Last night he was more than glad to punish Sissy – for me.  But he used his belt on him and he used it hard!  And he seems happiest about Sissy when Sissy is either enduring something horribly humiliating or horribly painful.  He thinks Sissy should get what he deserves – the more the better.” 

     Gloria nodded.  “So are you trying to avoid Derek in any way because of it?”

     Mel shook her head.  “No.  In fact, I think I keep finding myself wanting to see him.  But for now, I just can’t see him alone.  I need Sissy to be there too.  This bet means way too much to me.”

      “And how about Derek.  If you want to see him so badly, does he mean that much to you as well?”

     Mel was caught off guard by the question.  She had to think about it for a moment.  “I like Derek.  A lot!  An awful lot I think.  But…”  She shook her head.  “Right now he doesn’t mean nearly as much as wining this bet.”

     Gloria had guessed that.  In a way, she was sorry to hear it.  But it was the answer she would have guessed.

     Chad approached the gym door with a mix of trepidation and anticipation.  He was anticipating it, because he knew for a fact that he had managed to orgasm last night from Mel just using his backside.  The trepidation however was because he never knew what other humiliating thing he would be up against.  But if Cassie played with him again today – like he hoped she would, maybe now that the ice had been broken again last night by Mel, he would be able to orgasm again from Cassie’s playing.  If… she played with him again.  The thought of the receptionist changing him instead briefly crossed his mind.  She hadn’t changed him all week – yet.  That little embarrassment was getting way overdue!

     As he reached for the handle to open the door, he caught a tiny glimpse of his reflectin in the glass.  He was dressed normally again – for him.  His dress was back in place and the stupid hair bow Robin had made him wear backwards was gone.  He was once again dressed in the least humiliating way he possibly could be – anymore. 

     He opened the door and went inside, noticing the broad smile on the receptionist’s face.  That wasn’t a good sign!  He curtseyed – because he knew he could never get away with not doing it.  “Hewwo, Thindy,” he said in his sissy voice.  “Can you pweathe get Cathy fow me?”

     Cindy giggled.  It always sounded like he said Cathy instead of Cassie, but then the way he had to speak, they were basically one and the same.  But she ignored his question so she could speak with him for a few moments longer.  Cassie still wouldn’t let her change his diapers again yet, but that didn’t mean she couldn’t tease him a bit.  She leaned over the counter with excitement in her eyes.  “I couldn’t believe that outfit you wore yesterday!  I loved it!  But tell me, did you enjoy wearing it?  Cause I got to tell you, it looked like a really fun outfit to wear!”

     Chad had to think about that a bit.  “Yeah, some,” he admitted.  “But it was trouble too.  Lots of trouble!”

     Cindy giggled.  “Yeah!  I saw your diapers sticking out below your skirt.  I still can’t believe they got that way!”

      “That wasn’t the only problem,” Chad said.  “I got molested on the way back to work.”

     Cindy’s eyes went wide in shock.  “You’re kidding, right?  I mean… what do you mean by molested?”

      “I stopped at a store to buy some water and three guys grabbed me and tried to force me into their car at the end of the parking lot.”

     Cindy just stared at him.  “You’re not kidding, are you!”

     Chad shook his head.  “No, I’m not.  It happened.  Now will you please…”

      “No, wait!  So what happened?” Cindy asked.

      “The police showed up while they were dragging me down the sidewalk and chased them away.”

     The still wide-eyed Cindy had to ask.  “And what did the police say?”

      “They only asked if I was alright.”

     Cindy shook her head.  “Wow!  I’d be so scared!”

      “I was so scared!” Chad told her.  “Now would you…”

     Cindy held up her hand.  “Yeah, I’ll get her.  But her eyes were still locked on him in amazement as she started to slowly move.  Molested!  Three guys!  The police!  She’d be…  And then something about him caught her eye and she stopped and stared at it for a moment.  She came fully out from behind the counter to see him better.  She didn’t ask, she simply went up to him and grabbed his wrist and held it up so she could see his fingernails better.  And her jaw went wide with surprise, but only for a moment.  Her mood at hearing how he had been molested was quickly replaced by the joy of seeing SISSY spelled out on his fingernails.  And she laughed!

      “I love it!” she screamed.  “It’s so perfect for you.  I was too preoccupied with other things about you the last few days to really notice your nails.  Do you like them?”

     Chad wasn’t sure how to answer that.  On one hand, he found them horribly humiliating – which he loved, but on the other hand he simply found them horribly humiliating!  “Um…” he said searching for an answer.  “I guess they’re okay.”

     Cindy giggled, her voice dropped almost to a whisper.  “Do you find them embarrassing?”

     Chad ignored her question.  He needed to get his diapers changed.  “Will you please get Cassie for me?” he asked again.  “I’m afraid I’m going to leak all over the place if I don’t get changed soon.”

      “Are you that bad again?” Cindy asked in wide eyed curiosity.  “Can I see?”  Without asking she reached down and pulled up the hem of his dress, exposing his now overly bloated all-in-one girdle.  “Oh poo!  You’re not wearing the same girdle as yesterday.  I can’t see them!”

     Chad stepped back a bit and pushed his dress down.  “Please,” he said.

     Cindy finally nodded and left to find Cassie.

     Chad stared after her.  Yes, he was very embarrassed by having sissy spelled out on his nails, but today, he could have cared less about Cindy’s reaction to it.  He really just wanted to get in to see Cassie and have his diaper changed.  And… if she happed to be in the mood to play with him again…  Well, he really hoped she would!

     Five minutes later, he was back in the tiny office again undressing while Cassie pulled his things out of the diaper bag for him. 

      “Hey!” she said as she pulled the sixth bottle out of the bag.  “Every one of these is empty!  What happened?”

     Chad blushed, even though he really had no reason to.  “Robin had me drinking them all morning.  It was way too many bottles.  I guess she forgot to save one for you.”

     Cassie shook her head and got to her feet with one of the empty bottles.  “Well we can’t have you going without one,” she said.

      “But I drank so many this morning!” Chad complained.  “I’m sure Mel wouldn’t mind if we skipped it just this once!  Besides, this afternoon I…”  But he stopped himself right there.

      “What about this afternoon?” Cassie asked.

      “Robin told me to buy three of the largest size drinks with my lunch today and bring them back to the office.  That’s way more than six baby bottles can hold!”  He looked expectantly at Cassie.  “So you see, I really don’t need anything else!”

     Cassie actually considered it for a moment.  “Sorry,” she said as she headed for the door.  “I promised Mel.  And besides, I don’t know how much of those three drinks Robin will actually make you finish.”  She opened the door and left him to finish getting undressed while she went out to find a way to deal with the empty bottle.

      “Robin will make me drink all of them,” Chad said resignedly to himself as the door closed behind her. 

     When Cassie returned a few minutes later, Chad was clad in only his heavily bloated diapers and plastic panties.  He was relieved to see it was Cassie who had opened the door and not somebody else. 

      “Here,” she said as she handed him the now full bottle.  “I filled it with water from our stock bottles.”

     Already resigned to having to drink it, Chad took the bottle and laid down on the floor so Cassie could change him.

      “Wow, you really are wet!” Cassie said a minute later as she managed to peel the tight plastic panties off of him.  I guess Robin has been forcing the liquids on you.”

     Chad said nothing.  He didn’t think he needed to.  He simply continued to drink mindlessly from the latest in his never-ending string of baby bottles, mostly concentrating his thoughts on how he was going to manage to drink as much as he knew Robin was going to make him this afternoon.  They were not happy thoughts.  Since it took so much longer to drink from the bottles, he figured he’d be pretty much spending the whole afternoon with baby bottles in his mouth.  If he could even finish them then.

     Cassie carefully pulled back his overly sodden diaper.  She had to hold it up for a moment as she did so as she noticed a bit of pee still trickling out of his chastity device.  The moment she felt it was safe enough, she quickly pulled the wet diapers out from under him and slid the three new ones she had prepared under him again.  And as she let his legs back down, again she noticed a bit of pee coming out of him.  But the stream was so weak that she didn’t have to worry about pulling the diaper up to catch it.  She looked up at his face.  He was drinking his bottle and staring mindlessly at the ceiling while she worked on him.  Had he even known that he had just peed a little?  She had no way of knowing of course. 

     She took a baby wipe and carefully cleaned up his front side.  No reaction from his face at all.  For all the notice he seemed to take, she might not have been there at all!  Still watching his face, she grabbed his chastity device and started pulling on it a bit, trying to force a reaction to his tiny member trapped inside of it… but he still didn’t seem to notice what she was doing.  She cupped his balls and gently stroked them as well… and again, no reaction.  Didn’t he feel anything down there anymore? 

     Shaking her head, she said, “Okay, roll over.”

     Her words snapped Chad out of his dumb thoughts.  “Huh?” he startled.

      “I said, roll over!”

     Happily, Chad put his bottle down and rolled over so she could work on his rear end.  This was the part he was waiting for.  Would she play with him?  He was certainly hopeful.

     Cassie carefully cleaned his backside, then she started applying the lotion to him, spreading it over him and working it into his skin as her hands caressed that part of him.  Did he just let out a small sigh?  She kept going, now starting to play with her one finger against his tiny little hole.  Now he reacted.  There was no doubt about it that time.  Why was it that he no longer seemed to feel anything at all from his front side, the side he was supposed to react from, but he now seemed to be incredibly sensitive to everything happening on the other side of his body instead?  Oh well, hadn’t she herself been working on conditioning him to do just that?  Helping Mel to deny him his male reactions and replace them with… well… maybe not exactly female reactions, but certainly something closer to that than his normal male ones.

     She stuck her finger all the way inside of him and wiggled it around a bit before withdrawing it.  His backside tried to follow her hand back up, tried to find her finger after she had pulled it out.  She almost laughed to herself as she opened her desk drawer and pulled out her usual toy.  “Scooch your knees up, baby.”

     Chad could concentrate on one thing and one thing only, the delicious feelings Cassie was giving him in the place he wanted to feel them the most.  Delicious!  The minute he felt the tip of her toy applied to just the right place, he stopped breathing and tensed his body for the anticipated feelings he was waiting for.  He felt the pressure of her toy against him increase, and he totally opened himself up to receive it.  He felt it going in, just a little, then it went out again – but not all the way.  In, then out.  Back, and forth.  Going just a little bit deeper and deeper each time.  But he wanted more of it.  He kept trying to get more of it, but Cassie was only allowing him just so much of it at one time.  He would have to resign himself to what she was going to do with him and not what he wanted. 

     Further and further her toy entered him, the ribs on the sides of it adding greatly to his pleasure.  And finally, he felt her hand hitting his skin, signifying that she had buried its whole length up inside of him.  He shuddered just a bit, but it was a wonderful shudder. 

     Faster and faster now she pumped, and now he responded in kind, pushing and pulling as he had learned to do over the last two months.  More, more!  He wanted more!  Faster!  Harder!  He had to get there!  There was an end to this, a goal!  He knew it was possible to get there now.  He knew that for a fact!  But there was something missing again, something that was keeping him from getting where he wanted to be. 

     His mind wandered from the present to the past.  Even as he worked furiously to achieve what he wanted, his mind reverted to the memories of the night before – to the time when Mel had been doing this to him – with her strap on.  To the time when Derek had stood there and watched his total humiliation.  To the time when… but that was it!  That was the one missing ingredient.  Cassie was doing such wonderful things to him, but she wasn’t saying anything.  Mel talked to him as she did it.  Mel continuously fed humiliating thoughts straight into his brain.  The thoughts alone were the fabric his dreams were made of.  And coupled with the fantastic feelings of her strap-on, a monstrously humiliating thing in itself, it was more than enough to propel him over the edge. 

     But here?  Here he had the wonderful feelings, but nothing else.  Here, Cassie was quiet while she worked on him.  Here, he had no one relaying humiliating suggestions straight into his mind.  Here – he only had half the equation.  Here… he wasn’t going to get there.

     Defeated, he gave up.  It had been fun.  Tons of fun!  Fun he would gladly enjoy and look forward to every day.  But it was nothing but a desperate false hope.  Nothing more.  He wasn’t going to achieve his goal with Cassie.  He probably never would.  As much as he loved the feel of Cassie’s hands, he needed the full package instead.  He needed Mel… and the incredible things she did to him… and made him do.  He needed… it all.  He needed… Mel.

     Cassie watched him give up again.  Why did he try so hard?  She guessed she couldn’t blame him though.  To be denied the ability to have an orgasm… especially after being constantly sexually stimulated by everything he lived with and everything that was done to him.  It was a torture she herself could never endure.  But she had Sandy to help her with that.  And Sandy was more than willing to help her any time she wanted it.  But Sissy…  Once again she felt sorry for him. 

     She had noticed that all through his efforts he had again spurted little bits of pee several times out onto the fresh diapers below him.  Did he know he did that?  Again, no way to tell.  He certainly didn’t act like he knew it… or maybe he knew it and he just didn’t care.  Not that it mattered. 

     His bet with Mel would soon be over.  And there was a possibility that she herself might have to decide which of them won.  And the big question was… which of them did she prefer to see win?