Tuesday, August 2, 2022

Too Old to be Young - Chapter 19 – Part 3 of 3

 

Too Old to be Young

By Karen Singer

 

Chapter 19 – Part 3 of 3

 

“Hi Jim,” Jackie called early Saturday morning as she let herself into his house.

“Morning!” she heard Jim call back. 

She headed for his office, and the two met halfway.  “How are you this morning?” she asked.

“Horney!  Frustrated!”

She laughed.  “Perfect!”

“For who?”

“You!  Now let’s get you showered and changed.  I’m in the mood to do some cooking.  When you’re ready we’ll go back to my house and I’ll make you breakfast.  Sound okay?”

He was surprised by the offer.  “Sounds fine.”  At least it would only be to go to her house.

Once again he lamented the fact that she didn’t unlock his chastity device.  He wondered if she even had the key and figured that most likely she didn’t.  More than likely, Pam had it and Jackie couldn’t unlock him if she wanted to…which he already knew she didn’t.  As he washed off in the shower, along with spending more time playing with his locked-up member than usual, he wondered if there was any way he could call Pamela and talk her into letting him free…even for just a little while.  Somehow, he figured it wasn’t going to happen.  Oh well, on to the next thing.  Breakfast with Jackie this morning.  That was something different.  He’d had lunch and dinner with her, but not breakfast.  What was up with her today?

A few minutes later, wearing one of his thick nighttime diapers instead of a regular one, Jackie snapped the lock shut on his onesie and he was trapped in it as usual. 

“Why don’t you wear a skirt or something pretty today instead of what you usually wear,” Jackie suggested.  “You say you can’t get any fun, but I don’t see you doing anything else you enjoy either.”

“That’s not that kind of fun I was interested in,” Jim replied.

“Well wearing something fun anyway when you come over.  Maybe your little girl outfit or something.”

“What’s the use if I can’t get the other kind of fun?”

“Because…you said it’s fun,” she laughed.  “See you in a little bit,” she said, just before she left.

Wear something fun.  He realized she did have a point.  He spent more time ignoring all the things that used to give him so much pleasure than he did playing with those things.  In the end, he didn’t wear his little girl dress, but he did wear another dress along with his red high heels.  As he grabbed his purse to go over to Jackie’s house, he realized he didn’t care in the least if his shoes and fingernails matched his purse.  It was still embarrassing! 

For all the fuss Jackie had seemed to make over wanting to cook, all she had done was to make some eggs and bacon.  Still, he appreciated the effort, and it was a pleasant meal…even though he sat through it wearing a dress and high heels, none of which were any problem at all. 

After breakfast, he went home and spent the rest of the day wearing the dress and heels, and every time Jackie changed him she put one of his thicker night diapers on him.  By bedtime, he was hornier and more frustrated than ever.  But looming over all of it was what would happen the next day.  Sunday.  The day he was supposed to go out to eat with all of them…wearing a diaper and his red high heels, along with carrying a purse in his hands that now had bright red fingernails.  Sunday.  Tomorrow!

 

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No, the bedwetting hypnosis files he listened to didn’t do one damn thing…again!  He distinctly remembered waking up at least three times during the night when he had to pee.  At least he was able to go back to sleep quickly afterwards.  As he got out of bed Sunday morning, he again marveled at how soaked his diaper was, even though he had only wet it three times during the night.  He was sure now that he was peeing more each time than he thought, but then he had caught himself dribbling just tiny amounts a few times during the day now.  So little that he could barely feel it.  When he had woken up during the night, since he wasn’t controlling things and holding back, he could only conclude that was what was going on.  He was peeing, but once most of the pressure was off, he was simply dribbling smaller amounts than he could feel.  Was that progress?  He hoped so.

He waddled into the kitchen and got his coffee maker going, then sat at his desk to look though the internet for a while.  In the back of his mind, he never once forgot that it was Sunday, lunch with the girls day.  Lunch with his red nails and purse day.  Not to mention his red high heels.  How bad could it be?  He was already dreading it.  Jackie, Beverly, and Lisa were bad enough, but there were times when Pamela simply scared him.

When his coffee was ready, as always now, he poured it into one of his small baby bottles with the koozie around it and took it back to his desk where he continued to search the internet for anything interesting, all the while holding the bottle in his hand, and mostly keeping the nipple in his mouth where he chewed on it.

“Hello!”

Jim looked up at the sound of Jackie’s voice.  He had been so intent on looking at the internet, while worrying about lunch later, that he hadn’t heard her come in.

“Coming!” he called as he got up from his seat.  She was in his office before he got to the door.

“Morning, Jim,” Jackie said, taking in the sight of him, the onesie locked on over an obviously bloated diaper and the baby bottle in his hand.

“Morning,” Jim replied.

“Doing anything interesting?” Jackie asked looking toward his computer.

“Nothing at all,” he replied.

“Well maybe we’ll do something later that may interest you, while we’re out.”

“I thought we were only going to lunch.”

“That’s the plan.  That simple.”

“Somehow, I doubt that.”

Jackie raised her eyebrow at that.  “Come on, let’s get you cleaned up.”

Twenty minutes later, Jim stood still while Jackie locked another onesie on him, sealing shut part of what he would be wearing out to lunch in a little while.  Fortunately, it was the part that nobody would see.  He hoped.  For some reason, Jackie had insisted on putting one of his thicker night diapers on him today under his onesie.  He prayed it wouldn’t show under his pants.  Everything else he was wearing was going to call enough attention to him.

“Twelve o’clock,” Jackie told him.  “Lisa is picking us up today.  We’ll all go in her car.  Don’t forget your heels.”

“I won’t,” Jim replied, frustrated at the thought of it.  Ugh!  Red high heels out in public.  Red fingernails out in public.  And carrying a purse with red in it out in public.  What could he wear today that would help disguise all of it?  He didn’t have a clue.  He chose the best pair of pants he could and a plain button-down shirt.  Did his pants hide his diaper enough?  So far, he hoped so.  He also hoped he wouldn’t wet himself too much before he had to leave or that diaper was going to be more difficult to hide.  Fully dressed and knowing he was going out soon, he automatically wanted to reach for his wallet and keys to put them in his pockets, except he couldn’t.  According to the rules of the agreement, he could no longer put anything in his pockets.  Everything was already in his purse.  His purse!  Just the thought of it made him queasy while at the same time it made his cock want to twitch inside his tiny chastity device, which it had no room to do.

 

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Ten minutes before twelve, Jim grabbed his purse and stood in front of his full-length mirror.  He was still trying to fathom going out somewhere dressed the way he was.  His fingers, his purse in his hand, and his shoes were all red…female.  The rest of him was not.  What had they turned him into?  What had he become?  The answer was simple.  Just what he had wanted all along.  He had just never planned on the reality of it ever being possible.  And now look what he was doing.  As he stood staring at his reflection, he had no choice but to consider everything.  Yes, he was going out dressed like…he didn’t know what, but at the same time, there was no denying how exciting it all was for him.  Incredibly exciting.  He just really, really wanted to do something about that excitement, but they had fixed him so that he couldn’t…until Tuesday night…or longer…depending on nothing more than a roll of a single die. 

A car horn honked from outside, with a sigh, he turned from his mirror and headed for his door.  The car in his driveway was already full.  He could see all four women inside.  Jackie opened the back door for him and he squeezed his body in, making it a tight fit.

“You’re looking more like one of the girls everyday Jim,” Pam joked as he closed the car door.  He could only wish!  What he looked – was embarrassing!

The women talked animatedly all the way to the restaurant, a place Jim had never been to before.  He noticed the moment they got to the parking lot that it was crowded and there were more cars pulling in behind them.  “Looks like we’re right in the middle of the church crowd today,” Beverly noted.

“We may have to wait for a table,” Jackie agreed.

Once Lisa had found a parking place, Jim did not want to get out of the car, but he did.  He did not want to walk to the restaurant, but he did.  He didn’t want to go in either, but he did.  The place inside was packed with a lot of people waiting, all of them looking him over.  He felt even more like a fool.  The women he was with ignored the way he looked.  Everyone else didn’t. 

“We’re going to have to wait a while,” Lisa told them after she talked to the receptionist.  “They don’t have a table for five available yet.”

“This place is always crowded on Sundays,” Pam replied.  “I was expecting that.”

With no place to sit, or hide, Jim had no choice but to stand around in the middle of everyone else.  Nobody spoke to him, fortunately, but they also never seemed to stop looking at him.  Was his face as red as hid fingernails?  He hoped not.  He judged it was over half an hour before they finally were led to their table.  Jim could do nothing but follow meekly along with the other women.  He was so glad to be able to sit down, and it wasn’t because of standing for so long in his high heels.  He set his purse on the floor where it wouldn’t be seen as easily and kept his hands in his lap as much as possible. 

Lunch took a long time.  None of the other women mentioned how he was dressed.  None of them mentioned his wet diapers under what he was wearing.  It was like there was nothing different about him at all.  He could easily tell that the other customers around him noticed him, but he did his best to ignore them all.  And finally, it was over.  He grabbed his purse from the floor and got to his feet with the rest of them and headed back to the car.  He was never so grateful to finally close the car door behind him.  He was especially grateful that Lisa was heading home.  Except she didn’t.

Nothing at all had been said, but once again he found himself in the parking lot of that same damn drug store, and all the women were piling out of the car.  Why were they there?  Why couldn’t they just go home?  But having little choice, he followed them into that same damn store.  They all seemed to wander around and shop, picking up skin care items and a number of different things.  Finally, they all headed to the checkout.  He stood back and waited, and a short while later he was back in the too crowded backseat of Lisa’s car. 

When Lisa dropped him off in Jackie’s driveway, he was incredibly grateful.  He had gotten through it.  He had been out dressed humiliatingly in public three times that week and he hoped he’d never have to do it again.  But in the back of his mind he already knew that every time he left the house from now on it would be the same thing.  Humiliation.  Because of an agreement he had made…that he had also made sure he couldn’t get out of. 

But more than wishing he could get out of that agreement, he wished he could get out of that damn chastity device.  That would make the whole thing a lot more worthwhile.  This was supposed to be all about him having fun, but the kind of fun he wanted the most just then was denied him. 

He was left with…frustration! 

And it was Sunday.  In two more days they were going to make his situation even worse.  But how much worse could anything get?  He wasn’t sure he wanted to find out, but he knew that in two more days, it would be…inevitable. 

He really needed some relief!

 

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