Too Old to be Young - Chapter 24

 

Too Old to be Young

By Karen Singer

 

Chapter 24

 

It was the irritating sound of someone talking in his ears that slowly woke him.  He grunted and pulled the annoying headphones off.  Once again he had managed to go all night with the damn headphones talking away.  If it hadn’t been for the fact that he was so used to the sound now that he could completely tune it out, he wouldn’t have gotten any sleep at all.  And there was no doubt about it now, the recordings he was listening to didn’t work.  He distinctly remembered waking up twice last night to pee.  He needed new recordings.  Better ones!

As he laid there, he assessed the situation with his diaper.  Just like it always was every morning now:  Bloated.  Bulky.  Huge.  Hot.  Soaked.  He had only peed in the thing twice last night before going to sleep, but somehow, only peeing into it twice more during the night didn’t seem to account for that much pee in his diaper.  But then he already knew the answer to that one.  He was dribbling a lot now.  So much that when he did pee, he was probably still dribbling a little each time.  He was sure that was the answer.  No big mystery there.

With a sigh he got out of bed and waddled his way to the kitchen to get his coffee maker going.  His usual routine.  With the question of his bloated diaper out of the way, his mind was free to think about the other thing that weighed so heavily on it.  He was going shopping again this morning.  He would be going out there into public, dressed…excruciatingly…like a…he didn’t know what.  A sissy?  No, somehow the word wasn’t strong enough.  But that was the general direction his thoughts were turning.

In truth, it had been a long time now since he had been able to go out his door and not worry about what everyone else thought about him.  And it seemed like week in and week out, Jackie and her demented friends only made that situation that much worse.  That’s why he was going shopping again today – to make his situation that much worse.  Because after today, he wouldn’t own any men’s pants anymore.  He’d be restricted to women’s pants and skirts only.  Female…from the waist down.  And he didn’t have a choice in the matter.  Thanks to his sick wishes, he, and they, had fixed it that way.  Stuck!

His mind still vividly pictured the raid they had done on his house last night.  After changing him at Jackie’s house, they had all come over and spent more time than necessary not only going through his closet, his hamper, and his washer and dryer, but the ladies had spent nearly half an hour looking at all the clothes he had – men’s and women’s.  They had even gone through every drawer he had and removed two pairs of short pants that he hadn’t worn in years.  Then, just before they left, Jackie had picked out one pair of pants from their stack of his pants and hung that pair on a hanger.  They were currently hanging prominently in the empty area of his closet where all his pants used to be.

He remembered something else from last night too.  Tonight, his meal of baby food would be at dinner.  But would Jackie invite him to have lunch with her too?  That seemed to be the way things had worked last week, although he didn’t know why.

When his coffee was ready, he poured some into one of his small koozie covered baby bottles and carried it into his office.  His long story was done.  Finished, but not finished.  Now it was time to read through the thing from the beginning and find out what he had.  Not to mention correcting the errors and problems along the way.  He pulled the story up, now completely put together into one document with twenty separate chapters.  He stuck his bottle nipple between his lips and began reading, sometimes tilting the bottle up a bit so he could drink, the rest of the time chewing on the nipple.  In minutes, he was mentally emersed in the story.  All thoughts of other things gone from his mind.

“Jim!” Jackie called as she walked through his front door.  Not getting an answer, she headed for his office.  “There you are!”

Jim was startled and looked up from his story.  “Jackie.  I didn’t hear you.”

“What are you doing?” she asked as she moved closer.

“Reading.”

“What?”

“The thing I wrote,” he told her. 

She noticed his empty baby bottle in his hand and took it from him.  Examining the new nipple on it told her everything she needed to know.  “Jim!  You’re chewing on these nipples again.  What did I tell you?  Where’s your pacifier?”

Exasperated, Jim got up from his chair and simply headed for his bedroom where Jackie noticed the pacifier on the night table next to his bed where she usually found it.  She picked it up and stuck it in his mouth.  Only then did she unlock his onesie so he could get a shower.  Jim was irritated that she wouldn’t be unlocking his chastity device as well.  Two weeks now with another week to go.  Or more!  Depending on nothing more than a simple roll of a single die, and so far, every single roll had been against him.  Obviously, the gods of chance didn’t like him much.

When Jim came out of the shower, since he knew they were going shopping soon, Jim wasn’t happy when Jackie put him in two of his daytime diapers instead of only one.  Somehow, the pantyhose over the diapers didn’t surprise him.  He was also surprised when she didn’t “suggest” he wear a bra.  But before he knew it, his diapers and pantyhose were locked onto him for the duration as she closed the lock on his onesie.

“Was there anything special you wanted me to wear today?” Jim asked sarcastically.

Jackie was delighted with the question.  “I’d really love for you to wear that little girl dress you have.  You really need more of them.  Or maybe one of your other dresses.  Or even a skirt outfit of some sort.”

“Then why did you leave me one pair of pants to wear last night?”

The question surprised Jackie.  “Because I didn’t think you would actually be willing to wear any of that when we go shopping today.”

“I’m not!” Jim told her pointedly. 

Jackie smiled and shrugged.  “It’s only a suggestion.  You asked what I’d like to see you wear today.  I told you.”

“Good!  Because I’m wearing pants!”

Jackie chuckled.  “For now.”  She headed for the door.  “Give me half an hour to get ready then come over.  We’ll take my car.”

Jim watched as she walked out.  All the things she had “suggested” he wear were nothing but ridiculous!  But then he realized the direction Jackie and her band of demons seemed to be going.  If things didn’t change soon, those “suggestions” might just become all he would have to wear.  He didn’t want to think any more about that.  He might wind up humping his bed uselessly…again.

 

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Jim was very aware that he was wearing pants.  Men’s pants!  He was also very aware that it was supposed to be for the last time.  That fact alone was blowing his mind.  They were going shopping just so he could buy himself more pants.  But they would have to be women’s pants.  Not only that, they were shopping so he could buy himself at least two skirts or dresses.  No, he couldn’t picture himself buying a dress in a store.  That’s what the internet was for.  He also couldn’t picture buying himself a skirt either.  For that matter, was her really going to go into an actual store and buy three pairs of women’s pants?  Damn his chastity device was hurting more than usual today.

Getting out of the car outside the department store was easier than he expected it to be.  Before he knew it, he was out of the car, carrying his purse and wearing his black heels where everyone would notice them.  He had a feeling the red nail polish he was wearing would be pretty easy to spot as well.  He had one hand carrying his purse, but he stuck the other one in his pocket.

The store didn’t seem to be busy at all.  Wednesday morning must be a good time to shop…for him.  He was relieved at the relatively few customers he saw.  Following Jackie around through the women’s department, looking at so many racks of women’s pants, he was very aware of the browsing she was doing…and even more aware of how much his chastity device was hurting. 

“Jim,” Jackie said.  “This is a good store to buy clothes in.  Why aren’t you looking?”

“Uh…I thought you were doing that?”

“I am.  For me.  And maybe you.  But you need to pick out some new pants to wear.  Not to mention some skirts or dresses.  Oh!” she suddenly said.  “Did you want to start with them?  I should have asked.”

“No!  No.  It’s quite alright.  This is…good.”  Actually, it was anything but good!

“Then start looking.  Pick something out so you can try it on.”

“Try it on?”

“Yes.  Of course.  You’ve got to see if it fits.  Oh, and no jeans!  I want you to have nice slacks.”

Nice slacks.  But Jim was having a harder time with the concept of now having to try everything on before he bought it.  Having little choice, he started noticing more about the pants he was walking past.  Some were shorter than others.  Some seemed to have wide legs.  Others were nothing but stretch material.  So many different styles, patterns, and designs.  And that didn’t even count the styles that were obviously made to accommodate larger hips than others.  Where should he start?  That answer came quickly.  With the basics.  Something as close as he could get to what men’s pants looked like. 

With a direction in mind, he began searching more actively.  So many styles, it was like getting lost is a forest.  He tried to find some that looked exactly like men’s pants, but with seemingly a thousand styles around him, he couldn’t find any.  Except some of the jeans, and Jackie had already flat out told him, no jeans!  Darn!  But even the jeans he saw didn’t really look very masculine.  But why should they?  All the pants around him were made for women.

Nice slacks!  Nice pants!  Huh!  For a woman maybe.  For him even nice pants would be an embarrassment.  He finally pulled a pair of black pants from a rack for a closer look.  No fly.  No zipper.  No pockets.

“Oh, they’re real nice,” Jackie noted as she came over for a closer look.  And they even have pockets.”

Jim looked closer.  “They do?  Where?”

“Here,” Jackie said as she inserted her finger into an almost hidden slit just below the waist band.  Jim stuck his fingers in it, but they didn’t go in very far.  “The pockets are so small they’re useless!” he declared.

“So what?  You can’t use them anyway.

With a frustrated sigh, he draped them over his arm to…try on.  Later!

“Black is a good color to have in your closet.  Now find some in some other colors or patterns.”

She was making things worse.  What was wrong with having three pairs of black pants?  Fifteen minutes later, he carried a pile of pants into the ladies’ dressing room.  Fortunately, there were no store attendants anywhere around.  Also fortunately, thanks to all the internet purchases of clothes he had already made, most of the pants he had chosen fit fairly well. 

In the end, he kept that pair of black pants that were a stretchy material instead of needing a belt…or a zipper…or anything else to hold them up.  Jackie also talked him into the maroon pair that had wider legs and did have a zipper in front, but no belt loops of course.  And finally, a pair in a houndstooth check pattern that Jackie liked…but he didn’t.  That pair also had no zipper, or belt loops, or pockets…or anything else.

“Can we go now?” Jim asked, ready to pay for the pants and get out of there.

“Not until you get some skirts…or dresses…or both,” Jackie told him firmly. 

He had been afraid she wasn’t going to forget about that little part.

As hard as Jackie pushed him to buy at least one dress, Jim held his ground…somehow.  When he finally set his purchases down on the checkout counter, along with his purse, he had added a black and white check pattern skirt that was straight and fairly tight all the way down to his knees, and a flowing patterned skirt that was lightweight and came down just below his knees.  The woman at the checkout counter looked at his purse, she looked at his red nails, and Jim could see she was thinking things about him that were anything but nice.  It’s a good thing she couldn’t see the diapers he was wearing under his pants.

It was a relief for Jim to get back into Jackie’s car.  It was a bigger relief to get back to her driveway.  It wasn’t a relief to hear what she said before they got out of her car.

“Go home, change out of those pants, put on whatever you want, then come back here and bring me those pants you’re wearing now.  I’ll start getting lunch ready.”

“Whatever I want to wear?” Jim asked.

“Yes, except those men’s pants of course.”  She smiled.  “I’d really like to see you in one of those skirts, but I’ll leave that choice up to you.”

With a sigh, Jim got out of the car and carried his bags back to his house.  As he took his men’s pants off he was very aware that he had worn them, quite possibly, for the last time.”  He looked at the pants and skirts that were now jumbled in a pile on his bed.  He tried each of the pants on again.  The problem he noticed with the stretch pants was that they seemed to compress everything around his diaper a lot more than he was used to, making him more aware than ever that he was wearing a diaper.  Would his diapers be more noticeable under them?  That was a big worry.  The problem he noticed about wearing the skirts, especially the loose flowing one, was that he couldn’t feel any kind of pressure at all around his diaper.  It was more like wearing almost nothing over it. 

Feeling brave…much braver than he should have, he wore the loose flowing pattered skirt back of to Jackie’s house.  Unfortunately, as soon as he got to the door, Jackie took his last pair of men’s pants from him, then sent him home again…to come back with his pacifier in his mouth.  Darn, the lady could be infuriating!

Lunch wearing the loose skirt was strange.  As many times as he had worn a skirt before, this one seemed to make him more aware than ever of what he was wearing.  When he went home after lunch, he kept the skirt on as he sat down to continue reading through his story.  When Jackie came later that afternoon, he put it on again after she changed him into just one single daytime diaper.  And he was still wearing it for his dinner of nothing but baby food later that evening.  All day he wore that skirt, right up until she came back from her Community Center Bridge game and changed his diaper just before bed. 

As usual, he laid down to sleep with the headphones on his ears listening to the hypnotic recordings to help him wet the bed at night (that didn’t work), and with a pacifier in his mouth.  Ten minutes later, as usual, the pacifier had to go, but he kept the headphones and the recording playing. 

His final thought before he fell asleep were that he no longer had any men’s pants to wear at all.  Only women’s clothes from the waist down.  Like it.  Or not!