Too Old to be Young - Chapter 17 – Part 2 of 2

Too Old to be Young

By Karen Singer

 

Chapter 17 – Part 2 of 2

 

Jim looked at the clock.  A quarter to three.  He had finished lunch a little while ago.  A much later lunch than he usually ate.  What time would Jackie show up to change him?  He wasn’t sure.  He was sure though that despite how wet he thought he was, with the super bulk of diapers he was wearing, he didn’t feel like he needed changing yet.  Besides, he hadn’t peed that much today.  But as he looked at the clock, he knew without a doubt that despite his diapers not being too wet, he was absolutely going to need a diaper change before long.  It wasn’t the wetting that was going to be his problem.  It was going to be a problem of a much messier nature.  Not to mention smellier.

He briefly wondered how nasty the smell would be being confined inside two of his nighttime diapers.  Not that he cared about that so much.  He just knew that since he was still doing everything possible to not hold back on his peeing and pooping, it was going to come out of him before too long.

Ten minutes later, he couldn’t concentrate on anything but the impending feeling of knowing he was going to mess his diaper.  He stood in front of the crack between the curtains on his back window and stared out at the yard behind his house, seeing it, but not seeing it.  He was doing everything possible to not tighten his muscles at all and just let it all happen naturally.  He’d had a bit of practice with it now.  Every single day lately.  The familiar pressure built, and before long, he could feel the mess sliding out of his backside, slowly at first, then faster for a moment until it slowed way down as it hit his diaper and nearly stopped.  But the mess was going to come out of him one way or another and the diaper was only a minor impediment to for it.  Faster and faster, he felt it all coming out, moving around, dropping down as gravity took hold of the worst of it.  He could feel it pressing against his backside, and he could fee it in the bottom of his diaper. 

He stood there, not only unwilling to move, but unable to move.  How bad was it this time?  It had felt like a lot.  It had all come out of him easier this time too.  Of course, with the thickness of the two nighttime diapers keeping his legs further apart, maybe that had a tiny bit to do with it too.

With the entire experience now over with, he finally pulled himself together and turned awkwardly around, being careful with the way he moved because of the huge mess he was now wearing.  He looked at the clock again.  What time was Jackie going to come and finally change him?  She had come over to change him earlier, but hadn’t because he had been sleeping.  Hopefully, now she would come sooner rather than later.  So what time was it going to be?  How much longer?

He didn’t walk.  He couldn’t.  He waddled instead, slowly and carefully around his living room for a while, often stopping to stare out the crack between the curtains.  He walked to his office, his bedroom, his kitchen, and back to his living room.  No Jackie.  No change yet.  It felt like he had been walking around his house forever!  He was getting tired of it.  He remembered sitting down in the mess yesterday.  In his recliner, it hadn’t been a real problem.  He also remembered sitting in the mess yesterday at his desk.  That had been…uncomfortable but interesting as well.

Remarkably, the entire situation was keeping him very turned on.  He had purposely not gotten himself off earlier so he could enjoy it all…and he had.  Now, thoughts of humping his bed ran through his head again.  He gingerly headed back to his bedroom.  He started to climb up on his bed so he could start humping, then he stopped himself again.  He didn’t know when Jackie would show up to change him.  Hopefully it would be soon.  What if she showed up while he was trying to hump his bed?  He’d much rather she didn’t see him doing that.  Darn! 

He turned and left the bedroom.  What was he going to do?  He supposed he could sit in his recliner and read again like he had done yesterday, but the truth was, he was now too turned on to read anything but fun stuff.  He headed for his desk instead.  Most of the mess inside his diaper was now in his crotch.  The thickness of the diapers were keeping his legs splayed wider than usual, and he now had even more reason to not close his legs.  As he sat down in his desk chair, he could still feel some of the mess squishing down and spreading out over his backside.  Yuck!  He couldn’t help it, the fact that this is exactly what he had asked Jackie to do to him, oddly enough, was keeping him very turned on.

He turned his attention to his computer.  Did he want to read something interesting?  But he was too turned on for that.  All he really wanted to do was to hump his bed – finally!  But he dared not do that in case Jackie showed up – soon!  So what did he want to do?  Not knowing, and not wanting to move around much, he pulled up the hypnotic files and started with the first one.  Only one at a time this time.  And hopefully, he wouldn’t fall asleep again.  After sleeping so long earlier, he could see no possibility of that happening at all.

When was Jackie going to get there?  He needed changing…and as soon she left, he needed relief!

One file.  Two files.  Which one was better?  They were both…okay.  He listened to the third.  Where the hell was Jackie?  He made small notes about each file he had listened to already.  He played a fourth file, then deleted it.  Terrible!  Where was Jackie.  He checked the time.  She had to be there soon.  He played two more files, deleting one of them.  Where was Jackie?  It was dinner time, and he was getting hungry.

He got up from his desk and waddled slowly and carefully out to his kitchen.  Where was that blasted woman?  Damn her!  He needed changing, not to mention a very good shower now.  He had been stuck in messy, smelly diapers for hours now.  Fortunately, with the two super thick diapers he was wearing along with everything else he was literally trapped in, he couldn’t smell it that much.  Fortunately!  Where was that blasted woman?

He finally grabbed his cellphone and called her.

“Hello?  Jim?” Jackie’s voice came over his phone.

Was she laughing?  Jim wasn’t sure.  “Jackie,” he said.  “When are you going to change me?  I need a shower badly.  I have for a long time now.”  And then he was heard it for sure.  There was no missing it.  The damn woman was laughing at him.  Ugh!

“Oh Jim,” Jackie laughed.  “Sorry, but I’m not changing you today.  Maybe at bedtime, but not until then.  Maybe!”

“What?  But I’m messy!  Disgustingly messy!  I need to be changed.”

“Not today,” Jackie laughed.  “I know those two super thick diapers can hold a lot.  So since you’re enjoying yourself so much with them today, I thought I’d let you enjoy them as long as possible.  Have fun today Jim.  See you at bedtime.  Bye-bye!”

Jim was suddenly holding his phone to his ear, with nobody on the other end.  One thing had come through perfectly clear.  She wasn’t going to change him.  Not until bedtime…and maybe not even then.  And with his onesie locked on, there was no way he could do one single thing about it.  He was stuck!  Stuck in his diapers.  Stuck in the mess inside his diapers.  Stuck in all the pee in his messy diapers.  Stuck in his bra and his white tights.  Stuck in his locked on little girl shoes.  Stuck in all of it!  Stuck!

He put his phone down and waddled straight to the bedroom.  He climbed up on the bed and began humping for all he was worth.  Forget the mess in his diapers.  Tough shit if it got all over the place.  He needed this!  He humped as hard as he could for almost five minutes before he stopped and slammed his fist against his pillow.  Damn it!  Damn it!  Damn it!  His diapers were so thick he could hardly get enough pressure against his cock to do anything.  The thickness of his wet and messy diapers were literally preventing him from getting any release.  He desperately humped slower now, still trying for anything he could get.  He tried bunching a pillow up and putting that between his legs to hump.  No luck.  In fact, it made it worse.  He looked around the room for anything he could put between his legs to try and hump and didn’t see a single thing.  He literally growled his frustration.  Damn that woman!  What had she done to him?”

After twenty minutes of desperate trying with absolutely no results, he gave up.  For all the good it had done him, he might as well have been locked up in that damn chastity devise again.  No!  Not that!

As he waddled his way slowly toward the kitchen to make himself some dinner.  He could feel that the mess inside his diaper was now literally everywhere.  Front and back.  Fortunately, it was all still inside the diaper.  He hoped.  And the worst part was, there wasn’t a damn thing he could do about it.  He glanced at the clock again.  How long until Jackie came to change him at bedtime?  Hours!  What was he going to do?  With a sigh, he realized that there was only one thing he could do.  Endure it all.  He had no choice.  Once again, he remembered that no choice was exactly the thing that he had asked Jackie to do to him in the first place.  No choice.  Endure whatever she threw at him.

In the kitchen, he started a fresh pot of coffee, then searched his refrigerator for something he felt like eating.  Eating wasn’t what he wanted to do, even though he was getting hungry.  Humping his bed and getting off was what he wanted.  Unfortunately, it seemed he couldn’t manage that just then.  He was stuck making dinner for himself.  Eating that dinner.

And enduring what Jackie had done to him. 

Damn, he needed some relief!

 

Too Old to be Young - Chapter 17 – Part 1 of 2

 Too Old to be Young

By Karen Singer

 

Chapter 17 – Part 1 of 2

 

Thursday morning, Jim got up knowing that he hadn’t unconsciously wet his bed the night before.  Then again on Friday, he got up knowing it didn’t happen either, and both nights he had listened to a hypnotic recording before going to sleep that was supposed to help him wet the bed.  Obviously, the recording didn’t work, or it was a lousy one to begin with.  He wasn’t exactly knocked out by the contents of the thing, but at least it had been free.

Friday morning, he and Jackie again went grocery shopping together, this time he wore his low-heeled black pumps that he loved wearing so much.  While he was still embarrassed over it, he didn’t feel like the low black pumps were as noticeable as the red high heels.  In fact, since nobody had said anything to him about his red heels the week before and nobody was saying anything about the shoes he was wearing this week, he actually enjoyed wearing them out in public.  Getting away with it, or not getting away with it and at least nobody bothering him over it, made it all that much more exciting for him.  The stuff of his dreams.

When Jim woke up Saturday morning, still knowing he hadn’t wet in his sleep, he decided to ditch the hypnotic recording he had listened to for the last three nights and find a better one.  He knew he needed to give the recordings more time.  Weeks or months maybe, but the truth was, the recording he had been listening to had been pretty darn bad.  He had found a number of free ones on the internet.  It was time to pick something better.

He got out of bed and automatically headed to the kitchen to get his coffee maker going.  He barely glanced at the three baby bottles on his counter.  They were all still on his counter because he had never bothered to put them in a cupboard.  His fourth bottle was still on his desk in the office.  With the coffee maker brewing a fresh pot, he headed for his desk.  He never even paused as he felt himself peeing slightly.  The thought that he was doing it so easily and with only a few seconds notice excited him.  In the past few days, he had gotten much better at keeping all those muscles in his body completely relaxed.  In fact, the way they all were now felt completely normal to him.  He was hoping that before long, peeing with no control would feel normal too.  That thought had his cock growing again inside his diaper.

He sat at his desk and pulled up a web browser.  As the browser opened, his hand automatically headed for the baby bottle on his desk.  He stopped himself.  The coffee in the half-full bottle would be cold.  Because of having to drink from nothing but baby bottles now, he was winding up drinking less coffee, and coffee was the primary thing he drank all day.  Most days, coffee was the only thing he drank.

Desperately waiting for his coffee maker to finish brewing, he started looking for hypnotic recordings he could listen to every night to help him learn to wet himself in his sleep.  On the site he was on, there were a lot of them.  He selected the first one from the list and started downloading it to his computer.  When that finished downloading, instead of listening to it, he found the next one and started downloading that as well. 

While the file downloaded, he grabbed his baby bottle and headed back to the kitchen.  He dumped the cold coffee out and grabbed the fresh pot.  He started to pour it into the baby bottle, then stopped himself.  What he was doing was dumb.  Because he was stuck drinking from the bottles, he was drinking a lot less, and despite the insulating Koozie around it, his coffee continuously got cold.  He set the large size bottle aside and removed the nipple from one of the smaller bottles instead.  He filled it and screwed the nipple back on.  When he grabbed it though, the darn thing was too hot to handle.  He grabbed the other drink Koozie and stuck the small bottle inside.  The smaller bottle for some reason was slightly wider than the larger one and the koozie fit more snuggly, which was good.  But what wasn’t good was that the koozie was too tall for the small bottle.  The tip of the nipple barely stuck out above the edge of the koozie.  The solution to that problem came quickly and easily.  Grabbing a pair of scissors, he removed the bottle and trimmed the koozie down to a smaller size that just covered the bottle but not the top.  When he put the bottle back in, everything fit perfectly.  He picked it up and drank as he headed back to his desk…once again peeing slightly along the way.

As he downloaded hypnotic file after hypnotic file to his computer, he held the smaller baby bottle and drank from it often.  Before long, he finished it…something he had rarely done since he started drinking from the darn things.  He went back to the kitchen and refilled it.  Ahhh!  Hot coffee.  The smaller bottle was working out much better!  This time he didn’t pee as he headed back to his desk.

 

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Jackie used her key to let herself into his house, once again carrying her own mug of coffee with her.  “Hi Jim,” she called out as she entered.

“In here,” Jim called back.

Jackie found him in front of his desk.  “Writing again, or just reading?” she asked.

“Neither,” he said.  “Just…looking around.”

“Having fun though?” she asked, noticing the smaller bottle in his hands.

“I guess,” he replied.  The file he had been downloading finished and he closed down his browser and headed for his bedroom, more than ready for his morning shower.

When he came out, he found Jackie waiting for him, but the diaper she was holding surprised him.  “That’s one of my nighttime diapers,” he noted.

“Yeah,” she replied with a smile.  “I just thought you might enjoy something different for a change.”

“Different?”

“You…I mean we…are doing this for your enjoyment, right?”

“Uh…yeah,” he agreed hesitantly.

“Then lay down and enjoy it.”

Jim settled himself on his bed and let Jackie pull the thick diaper under him.  But she left it there and got a second thick nighttime diaper too. 

“Two?” he asked.

“Very good!” Jackie replied.  “For a big baby, you can count to two.  Congratulations!” 

Jim watched with wide eyes as she carefully grabbed a pair of scissors and started cutting slits in the lining all over the thing, especially in the crotch.  She had him raise his butt and carefully slid that one between his bottom and the first diaper she had laid out on the bed.  She tightly pulled the inner diaper around him and fastened it securely.  She had to work a bit harder to pull the second diaper tightly over top of the first one, but in moments it too was fastened securely.

Jim got up from the bed trying to come to grips with the ridiculous bulk between his legs.  Before he could make a comment about it, he found Jackie handing him something – his white tights.

“Here,” Jackie said.  “Put these on too.”

Jim was still trying to fathom the double night diapers he was wearing as he worked to pull the tights up his legs.  But of course, after that, Jackie handed him a bra to put on.  When it was in place, she stuffed the cups of it as full as possible with some of the things she found in his dresser.  Jim already knew what was coming next.  No surprise, one of his onesies soon locked every bit of it onto him so he wouldn’t be able to remove any of it.  And after that, came the locking little girl shoes.  Locked, of course.

“Might I suggest your darling little girl dress again?” Jackie suggested.  “But of course, what you want to wear over that is up to you.  That is, if you even want to wear anything over it.  With a laugh, Jackie turned her back to him and headed for the door.  “Enjoy yourself Jim.  I know I’ll be enjoying thinking about you.  How much fun is it to wear diapers that thick?”

Jim stayed in his bedroom listening to the sound of his front door opening and closing.  What did he want to wear…if he wore anything at all over top of what he had on?  He couldn’t decide.  Wear the fancy dress, or dress more normally?  Of course, he had other dresses and skirts he could wear too.  Still mostly concerned with the huge bulk between his legs, he couldn’t decide.  All he could think about was the feel of the thick diapers trapped under his onesie. 

He walked around a little bit in his room with his hand pressed against his crotch as he tried to get used to the massive bulk between his legs, pressing his thighs apart.  He couldn’t even close his legs! 

He had a feeling that wearing a pair of men’s pants might be out, not that he had any interest in wearing them anyway, he was once again too turned on by his situation.  Another situation he couldn’t get himself out of.  He looked at his bed, already picturing himself humping to get himself off.  He got as far as beginning to climb up on it when he stopped himself.  No!  He didn’t want to lose the feeling so quickly.  He wanted to savor it and enjoy it as long as possible.

Not knowing what he wanted to put on, he wandered back to his office where he automatically grabbed his baby bottle and put it to his lips.  After what Jackie had dressed him in…and locked him in…his legs were splayed uncomfortably in his seat.  His mind was practically blank with shock.  He sipped unconsciously from his bottle while waiting for his web browser to come up, he felt the now faint feeling that he was going to pee soon.  His mind latched onto it as something to concentrate on.  It happened only moments later, then the feeling was gone.  In the huge bulk of his diapers, the bit that he had peed seemed to make no difference at all.

Still sipping from his bottle, he put deciding on something else to wear out of his mind and found where he had left off earlier and started downloading another hypnotic file.  When he had twenty of them in his collection, he decided he had enough.  It was time to start weeding out the good ones from the bad.  He refilled his small baby bottle with fresh coffee and went back to his desk.  He pulled his headphones on over his ears and started listening to the first file. 

The continuous almost monotonous droning of the voice as it went through the lengthy induction process was boring beyond belief, even though he thought it was better than the file he had tried to use already.  He kept listening though because he needed to hear all of it so he could compare the contents with the other files in his list.  It felt like it took forever before the file finally finished and the next file in his list automatically began to play.  By the time he reached the end of it, his head was laid back and his eyes were closed. 

Why had he downloaded twenty files?  Yes, he was enjoying listening to them.  Actually, he was enjoying them when they finally got past the induction processes so he could hear the suggestion content, but he felt he needed to evaluate the induction part of them too.  Unfortunately, the induction for the recordings so far was most of the content.  At least it felt that way.  With his head back and his eyes closed, he fell sound asleep halfway through the fourth file.

 

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“Hi Jim,” Jackie called as she entered his house just before lunchtime.  She had come over, even though in reality, she had no intention of letting him change.  She had double diapered him in those thick nighttime diapers.  It was time for him to figure out that he wasn’t going to get changed today until much later…if at all.  In fact, if his diapers held up well enough, maybe she wouldn’t change him until bedtime.  She wasn’t sure about that.  She would have to see. 

Not getting an answer from him, she went searching for him and found him laying back in his desk chair with headphones on his ears.  She heard him snoring softly.  Should she wake him?  But what would be the point if he was enjoying a nap.  She had no intention of changing him anyway.

Feeling a bit devilish, she grabbed a pen and a piece of paper and left him a note telling him that she had been there, but since he was so sound asleep when she came to change him that he would have to miss this diaper change and wait until the next one.  With a small chuckle, she quietly left his house and went home.

 

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Jim felt groggy beyond belief as he slowly woke up.  His body ached from not sleeping in a more comfortable position.  There was the soft voice of someone telling him that he would wake up feeling very refreshed playing in his headphones.  Just then, refreshed was the last thing he felt.  He pulled the headphones off and set them on his desk.  In truth, he couldn’t remember much of anything he had listened to before he fell asleep.  It was all one big jumbled mess.  He shut down the file that was playing, not even knowing how far the system had gone.  He had fallen asleep in the middle of it all, so it didn’t matter.

Standing up, the unfamiliar bulk of his diapers was thick and heavy.  He felt hungry too, but he would wait until after Jackie came and changed him before he ate.  Grabbing his baby bottle, he headed to the kitchen to refill it.  Walking was even more uncomfortable than it had been earlier when Jackie had first locked him into it all.  But he knew it was all just from it being such a new experience for him.

He refilled his bottle and put it to his lips for a quick drink.  Ah!  Good and hot.  Taking another drink, he headed back to his office.  When he got there, he found the note that Jackie had left him.  She had been there?  He couldn’t believe it.  He checked the time.  Damn!  It was almost two in the afternoon.  How long had he slept?  No wonder he felt so groggy.  No wonder he was so hungry.  He sat down in his chair again, the unfamiliar bulk of his diapers momentarily feeling strange underneath him as he contemplated the fact that he had napped for so long.  As he sat, he stared at his list of hypnotic files.  Since he had fallen asleep listening to them, he couldn’t even remember which of the first few he had listened to were better than any other.  He was going to have to start again, and hopefully, this time, not fall asleep.

Frustrated, he got to his feet and waddled back to the kitchen to make himself some lunch.  How long before Jackie was going to come back to change him?  He remembered peeing a few times earlier, but he certainly didn’t remember needing to pee while he had been napping.  With the huge bulk of diapers inside his onesie though, he didn’t really feel like he needed changing yet.  Thinking about that, he once again felt the telltale signs that he was going to pee.  A few moments later, it happened.  Nope!  Didn’t pee while he was sleeping, not if that much came out of him now that he was awake.  As he had been doing all morning, he took another sip from his baby bottle.  Now, what did he want for lunch?

 

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Too Old to be Young - Chapter 16

 

Too Old to be Young

By Karen Singer

 

Chapter 16

 

He had been so exhausted last night by the time he got to sleep that he hadn’t bothered to listen to the hypnosis file he had downloaded the day before.  Despite his lack of sex for the last week, and despite his new situation of only being able to drink from baby bottles, it had taken more of a monumental effort than ever to hump his bed and get himself off.  And then there was the fact that trying to sleep while being still stuck wearing a bra and pantyhose added their own bit of discomfort.  Especially the bra.

Despite his exhaustion, he still knew it and woke up every single time he had to pee during the night.  At least he was fairly sure he knew it.  He had been pretty exhausted.  He glanced at the baby bottle in it’s koozie on his nightstand.  It was still half full from last night.  He grabbed it and took a swig.  Cold.  Yuck!  Those demented women had fixed it so that from now on he would be stuck drinking from only baby bottles.  At least as far as when he was home.  He didn’t see any way that they could do anything about what he would do if he went into a restaurant.  And he wasn’t planning on carrying a baby bottle anywhere with him whenever he left the house.  That at least was a bright spot.

He took another long swig of the cold coffee, then placed the bottle back on the nightstand.  Just the thought of being stuck drinking from it had him so turned on again that he couldn’t stand it.  Once again, he rolled over onto his stomach and did his best to hump his bed.  Just like last night, it took him forever.  But at least he got off, not to mention how much he had enjoyed doing it.  The only problem was that now that he was done, as usual, he wanted nothing to do with the baby bottles, or his diapers, or the bra and pantyhose stuck under his onesie.  He really wanted a shower now too, but of course, locked into the thing, he had no choice.  Thanks to Jackie, he had no way out of any of it.  His new life.

He was tempted to scream.  Instead, he got up and went to the kitchen to make more coffee, where he couldn’t miss all the baby bottles on his kitchen counter.  It was one thing after another.  Diapers, then the heels, now baby bottles.  One thing was for sure, Jackie…and the other women…weren’t making his life easy.  As per his usual morning routine, he set his coffee maker working.  Heading into his office, he was glad that at least he was done being forced to wear the heels all day.  He flexed his toes just because he could.

He pulled up his story and kept working from the point he had left off yesterday.  When his coffee was finished, he grabbed the baby bottle from his bedroom and carried it back to the kitchen.  He unscrewed the nipple and had to be very careful to pour the coffee into the small opening.  He screwed the nipple on and took a small swig.  At least this time it was hot.  But what a bother!  What the hell was he going to do?

With little choice, he carried the bottle back to the office where he went back to working on his story.  Because he could only drink from the bottle, he was forced to take small brief swigs of the coffee and at much greater intervals than he normally would with his usual mug.  Consequently, he was drinking far less coffee.  Something he didn’t realize until much later.

 

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It wasn’t that cruel…but Jackie did it anyway.  When she let herself into Jim’s house, she purposely carried a large mug of coffee in with her.  She certainly wasn’t about to drink any coffee from his baby bottles, and there was literally nothing left in his house now to drink from anyway.  But her carrying the mug of coffee in and drinking it in front of him was a tiny bit of cruelty to press that point home.  Besides, she couldn’t wait to see him pick his bottle up to drink from it.

“Hi Jim,” she called as she went in through the door.

Jim turned in his desk chair as she came into his office.  The mug of coffee in her hand wasn’t lost to him.  He looked at it for a moment, then purposely looked away.  Jackie spent the same amount of time looking at the baby bottle on his desk, before turning her gaze on him, taking in his “breasts” and pantyhose locked on under his onesie.  Cute!  She liked seeing them on him.  Especially when he couldn’t get them off.

“How’s it going?” she asked.

Jim shrugged.  “Fine.”

“Any problem with the bottles?”

“They’re hard to drink from.”

She noticed that the bottle on his desk was only partially full.  “But I can see that you’re managing.”

“So far,” he replied, once again looking at the large mug in her hand.

Jackie nodded toward his baby bottle.  With a cruel smile, she said, “I can’t wait to walk in here one day and see you sleeping, while that thing is still in your mouth.” 

The thought of it suddenly sent Jim’s cock lurching inside his soaked diaper.  He was tempted to say heaven forbid, but he held his tongue.  Was it possible that it could happen?  He seriously doubted it, but he did take naps during the day.

“Shower time?” Jackie asked.

“Please!” Jim replied as he got up from his seat.

Twenty minutes later, Jim had one of his semi-thin daytime diapers on, and they were “discussing” things.

“Jim,” Jackie said.  “Do you have any plans on going out somewhere today?”

“No.  None!  Unless you’re going to force me to do it.”

“Of course not.  Not this week.  We just need you to get used to drinking from those bottles all the time.  So why not wear them?”

Jim considered it.

“Jim,” Jackie said.  “This is all your fantasies.  This is all for your enjoyment.  Isn’t this what you wanted to do for fun?  Isn’t this why you moved here and was hoping to chase all the neighbors away so they would leave you alone to…enjoy yourself?”

Like it or not, Jim had to admit, she did have a point.  But what if he did want to go out somewhere?  He thought again about the fact that he now had only women’s shoes to wear, even out in public, and he banished all thoughts of leaving the house from his mind.  “Yeah,” He conceded.  “I do enjoy it.”

“Then put them on.”

Jim nodded and reached for the pantyhose he had been wearing all day yesterday and last night.

“No Jim!  At least get a fresh pair.  A fresh bra too.  And this time, stuff some panties or something in it to fill it out.  It’s your fantasies.  You might as well enjoy them all you can.”  She didn’t add – while you still can.

Ten minutes later, Jackie snapped the lock shut on the back of his onesie, sealing his diapers, white tights, and stuffed out bra inside it so he would be stuck wearing them all day.

“Now what else are you going to wear?” she asked.

“I don’t know yet,” Jim replied as he headed for his closet. 

“Can I make a suggestion?”

“What?”

Jackie went to his closet and pulled out his one dress that was the most outrageous.  His dress that looked like something a little girl might wear – fifty years ago!

“That?” Jim exclaimed.

“Jim, you’re stuck wearing and using diapers like a baby, now you’re stuck drinking from baby bottles.  Personally, I think it’s only fitting.

Jim looked at her skeptically, but his cock was now going crazy inside his diaper.  Besides, he could take it off and put something else on – just as soon as she left, and he managed to get off humping his bed once again.  He still had a week’s worth of non-sex to make up for.  With her watching, he put the dress on, doing everything possible to not let her know how turned on he was.  But once he had it on, she was holding out his shoes for the day, the locking little girl black flats with the big white bows on the toes.  Wanting her gone more than ever, he put the shoes on and let her lock them, taking the keys.

With a laugh, Jackie headed for his door.  “Enjoy yourself Jim.  I just know that you will.”  With another laugh, she was gone, and Jim immediately headed for his bed.

The dry thinner diaper helped, maybe so did everything he was wearing, but once again it took a while for him to get himself off.  But as always, once he did, he wanted out of everything he was wearing, except that this time the only thing he could possibly remove was his dress, and that was it. 

Finally deciding it was no use changing, wearing the little girl dress, he went back to his office.  He took a swig from his baby bottle.  Ugh!  Cold!  He went into the kitchen, dumped it out and poured himself a fresh bottle of coffee.  Putting it to his lips, he drank deeply.  As he walked with it back toward his office, he once again forced himself to make sure his bladder muscles were as relaxed as possible, something that he had forgotten about earlier.  His muscles had been loose, but not completely relaxed.

He looked at the story he was working on, but decided he wasn’t interested in it just then.  He headed for his living room instead and grabbed his tablet with the story he was currently reading from it.  A story that would do nothing at all for any of his sexual fantasies that just then he had no interest in at all.  He sat back in his recliner and raised his feet.  The white tights and big white bows on his locked-on shoes couldn’t be missed if he tried.  He grabbed the sides of his skirt with both hands and stretched it out wide.  Finally, he opened his tablet and turned to the story he was reading…and did his best to forget his current life and get lost in someone else’s problem.  It took him a while.

It was a while before his story was interrupted by the faint brief feeling that he needed to pee.  He stopped reading and concentrated on not stopping it in any way so that it would happen naturally.  He loved it, despite the fact that it was over with far too soon.  Once done, it took only moments to get back into the story again.

 

--- §§§§§§§§§§ ---

 

Jim’s phone rang.  He had read for a long time and was now just lying back in his chair with his eyes closed.  Relaxing.  The sound of his phone startled him.  He hurried up from his seat and found the thing.  “Hello?”

“Hi Jim,” Jackie’s voice came back.  “How are you doing?”

“I was doing fine,” he told her.  “I was almost asleep.”

“Oh.  Sorry,” Jackie replied.  “Listen,” she said.  “I was just making a batch of chicken salad for lunch and wanted to know if you’d like to come over and have some with me.  And if you bring a fresh diaper with you, I can change you right here.  What say?  Feel like some company for a little while?”

Jim considered it, then remembered what he was wearing.  He glanced down at the skirt of his dress, seeing his white legs and the shoes attached to his feet.  “Uh…maybe not,” he told her, not wanting to go outside his house the way he was dressed.

“Why not?” Jackie asked.

“Uh…not a good idea today,” Jim replied.

“Why?  Because of what you’re wearing?”

“Yes!”

“For heaven’s sake Jim.  Who’s going to care?  It was your fantasies remember.  Just get over it…and get over here!  Oh, and don’t forget to bring a fresh diaper with you.”

Jim fumed a moment.  Was she ordering him around again?  Making him do things that weren’t part of their agreement?  Or was it just lunch?  But it was just next door.  If he hurried, maybe nobody would see him.  Besides, Jackie didn’t have any baby bottles at her house…he hoped.  It would be a chance to drink from something normal again.  “Fine,” he replied.  “I’ll be there in a few minutes.”

“Good,” Jackie replied happily.  “See you then.”

Jim set his phone down.  Ugh!  Now he would have to brave going outside, dressed as he was.  He went to his room and the latest package of diapers he was pulling from and grabbed one.  He grabbed his keys in his hand too so he could get back into his house and was heading for his door when his phone rang.  He found it and answered it, noticing that it was Jackie calling again.  “Hello?”

“Jim,” Jackie said.  “I almost forgot.  Don’t forget to bring one of your baby bottles with you.  If you don’t, you won’t be drinking anything at all.  See you in a few.”

Jim never got in a chance to say anything.  Damn the woman!  She was making sure that even at her house he would be drinking from those darn baby bottles. 

He grabbed a fresh one from his kitchen counter and stuffed the empty bottle into one of the koozies.  With his hands fairly full, he went out through his front door, and literally ran the short distance from his house to hers.  He fumed at how long it seemed to take her to answer her door, but finally it was opened, and he hurried inside.  Whew!

Jackie smiled.  “My, don’t you look absolutely sweet in that dress.  I just love it.  Everything you’re wearing in fact.  You really ought to wear it more often.”

Jim said nothing, knowing she was teasing.

“Coffee?” Jackie asked as she held out her hand toward the baby bottle he was holding.

It was a moment before Jim handed it over.

“How come that’s the only fancy dress you have?” Jackie asked as Jim followed her toward her kitchen.

“What do you mean?  I’ve got other dresses.  A few of them.”

“But nothing like that.  I mean…the silly little girl style.  I would think you would own a few of them.  You got that one for fun, didn’t you?”

“Yeah,” he admitted.  “But I haven’t been at this very long.  Really, only since my wife died.”

“Oh, that makes sense.  But you ought to consider getting yourself a few more.  Like I said, it really does look so sweet on you.”  She filled his baby bottle with coffee, screwed the nipple back on and handed it to him.  She was disappointed when he didn’t immediately put the thing to his lips to drink.  “Ready for lunch?” she asked.

Jim had to admit, she made a mean chicken salad.  He was enjoying it a lot, the conversation…maybe! 

“So tell me Jim,” Jackie said at one point.  “And I mean honestly.  How bad was it last week when you were stuck in that tiny little chastity device?”

“Tiny is right!” Jim agreed.

Jackie chuckled.  “But how bad was it really?”

“Uh…frustrating!”

“I’m sure it had to be.  I’m guessing that’s the whole point of those things.”

“Yeah.  For sure.  And it was.”

“But what I’m’ trying to get at is…was there anything about wearing it that you found…uh…enjoyable?  Like you enjoy being stuck in your diapers and forced to use them. And Jim, please, answer honestly.”

Jim had to consider the question for a moment.  “Yeah,” he finally admitted.  There’s no doubt that the situation itself fueled my fantasies.  And not being able to get off kept me interested in everything.  Maybe a bit too much.  Having no control at all over being unable to get out of it didn’t hurt either I guess.  So overall, I guess, yes.  I enjoyed it.”

Jackie nodded.  “Thought so.  Maybe someday we’ll try it again.  Especially if we find any reason to punish you!”

Jim came close to shuddering.  “Heaven forbid!” he muttered.

“So,” Jackie said, suddenly changing the subject.  “What are the chances of you buying any more fancy dresses like the one you’re wearing?”

 

--- §§§§§§§§§§ ---

 

Less than an hour after Jim got back from lunch and being changed at Jackie’s house, he knew he was going to have a slight problem.  It was much earlier in the day than usual for it to be happening.  He was still trying had to keep his body as relaxed as possible so he could pee and poop whenever the need hit without any conscious intervention at all, but now it was much earlier in the day than usual, and he already knew that if he continued doing what he had, then he was going to wind up with a stinky, messy diaper very soon, and he had only been changed just before he came back from Jackie’s house.  He didn’t usually do this until later in the afternoon.

Should he, or shouldn’t he?  Should he continue to try and play like he was completely incontinent and unable to control himself, or for once, hold it!  He didn’t really want to be stuck in a stinky, messy diaper for the rest of the afternoon.  And standing up so he wouldn’t have to sit in it would be even more irksome.  So what should he do?  He could already tell that he was going to have to make his mind up about it pretty quick, or he would…. 

He realized too late that the decision had been taken away from him.  He should have tightened his muscles back there to hold back, but now he could already feel that a tiny bit of what was trying to come out of him, had already reached the point where it was coming out of him.  Damn!  Figuring he had no other choice just then, he stood there and continued to keep his muscles as relaxed as possible.  The process seemed to take forever, while at the same time, it didn’t.  Before long, he had a load in the bottom of his diaper.  Damn!  Now what was he going to do?  It was going to be hours before Jackie came back later that afternoon to let him shower and change.  Hours!  Ugh!

He stood in front of the crack between the curtains of his back window and looked out at the yard.  Why had it happened so much earlier today?  Maybe it had something to do with the fact that for days now he had been purposely trying not to hold back.  To play at being totally incontinent.  Another possibility came to mind.  Had Jackie somehow “spiked” that chicken salad?  But no, she had eaten from the same bowl.  Of course, chicken salad was made with mayonnaise, and mayonnaise was full of oil.  Did that have anything to do with it?  Or was it possibly a combination of that and not holding back for the last few days?  He had no way of knowing.  All he knew was that he was now stuck, locked, into a messy diaper. 

A few minutes later, to add insult to injury, he peed into the thing too.  Great!  Just what he didn’t need.  But at the same time, it also excited him.  Enough that instead of standing at his window, he headed back to his bedroom where he again humped his bed for a very long time before finally getting off.  And of course, as usual, once he got his load off, he would much rather be done with all of it.  Unfortunately, for the last few weeks now, he’d no longer had a choice in the matter.  He had no choice in being done with any of it.  He was stuck…because of that damn woman and her friends.  Never mind the fact that he had asked her to do it to him, that he wanted it. 

He sighed deeply as he gingerly got up from the bed.  He could feel the weight of his diaper and the load in the bottom of it.  His onesie was tighter in the shoulders now that usual because of it.  He walked back out to stare out his living room window.  How long until Jackie came?  Hours!  Damn it!  He didn’t want to stand there that long.  He headed for his recliner and slowly, gingerly, settled himself down into it.  It wasn’t so bad.  With the mess now in the very bottom of his diaper it didn’t feel like he was sitting in too much of it.  Noticing the odor more now than ever, he picked up his tablet and began reading again.  Maybe he shouldn’t have gotten himself off so soon.  If he hadn’t, maybe he’d be enjoying his situation a whole lot more. 

His bottle of coffee from that morning was on the table next to him.  He picked it up and took a swig.  As he expected cold!  Awful.  He would have gotten up to make some fresh coffee, but he didn’t want to have to get up and then sit down again.  He stayed right where he was and read instead, trying to let the story keep his mind off of his problems.

He read several chapters before he found his mind wandering.  But what it wandered to was much more interesting than his book.  Jackie had suggested that he buy himself some more little girl dresses like the one he was wearing.  Actually, he had found it on a site that sold them for adult babies.  Should he get another one?  Did he want to?  The more he thought about it, the more he realized that he did want another one.  The question was, did he want to get out of his chair and go into his office to look at them on his computer, or was he better off staying seated right where he was?  If he stayed where he was, he wouldn’t have to worry about sitting down in his desk chair with that load in his diaper.  On the other hand, he really did want another cup of coffee.  Or in this case, a damn baby bottle of coffee.  Ugh! 

He gingerly got out of his recliner and headed for the kitchen to get the coffee maker busy.  Only after it was finished, and he had filled one of his bottles did he brave going into his office where he carefully sat down.  Ugh!  Messy!  But there was no doubt about it, it was better than standing up all afternoon. 

He got into his computer and a minute later was looking at baby dress after baby dress.  He had just humped his bed a few hours earlier, but his cock was certainly enjoying its newfound freedom inside his diaper.  He was glad that chastity device was gone!  Hopefully, for good! 

Once again thinking about that fact, he gave up on looking at dresses on the internet and went into his bedroom where he once again humped his bed.  And of course, the only problem after that, was after he was done, he was no longer interested in anything except getting out of his predicament…which of course, was impossible. 

There was just no winning!