You bet your life!

by: username | Complete Story | Last updated Apr 21, 2021

Jefferey gets a do-over. I wanted to do a grittier story this time around.

Chapter 1
On fetishes and lost opportunities...

Chapter Description: Life is often messy. (This is why we call it "life" and not "messy")

 You bet your life!

Coming home from yet another long, dull day of work at the office, Jeffery turned on the tube, scanned the channels for something of interest, and settled on a kid’s cartoon.

In the cartoon, the hero characters had to deal with a villain that planned to take over the world with his “youthalizer” gun. Half of the characters ended up as toddlers in diapers and were taken care of in a nursery.

Youthful antics ensued complete with pee-pee and diaper soiling underlining the juvenile humor that was a hallmark of the cartoon series. The toddlers broke out of the nursery and aided the grown-up members of the team to beat the villain and subject him to his ray while aging up the toddlers back to their normal ages in the process.

Jeffery watched the cartoon with rapt attention, feeling little thrills up and down his spine and rubbing his erect member through his business suit staining his underwear with precum in the process.

Wanting more, Jeffery scanned the channels and didn’t find any more shows with age regression in them. He felt even more frustrated and went to his bedroom, undressed, and pulled out his ABDL gear which consisted of a thick adult diaper, an adult onesie, and a size 5 Nuk pacifier. After powdering up and donning the outfit, Jeffery went to his computer to find more Age-regression cartoons.

As he searched the webs, he found several sites that gave information on cartoons with the desired subject and then found several of them on Eew! tube which he watched and slowly pleasured himself via diaper rubbing.

After nearly making it to climax, he realized that he was thirsty and downed several beers while looking for more age-regression fap material on the webs.

In his search, he found an odd website called “Return to diapers” with lots of good fuel for his self-pleasuring. The beers that he consumed now wanted out and his bladder signaled its urgency for release. He let it out and flooded his thick adult diaper with the nice warm feeling of urine.

This enhanced his self-pleasuring and allowed the sexual release that he desired. He cummed a load into his diaper and reclined back in his executive chair in the afterglow, his sweaty body starting to itch in certain locations.

After recovering a bit, he decided to see what else the site had available and came upon a link that said: “Discover a new you, rewind your internal clock” with a flashing arrow next to it.

“Ah, why not?” he said aloud and pressed the link.


His bedroom disappeared and he found himself standing in a gray waiting room with gray chairs, gray walls, and gray carpeting. A gray receptionist pointed to a ticket dispenser that had a sign above it saying “Take a number”. He took his number and sat in one of the gray chairs still wearing his soggy ABDL gear.

After a short period, a bell chimed and his number was called out and the receptionist got up and opened the gray door motioning him in.

The office that he was ushered into was every bit as gray as the reception room. A gray man in a gray suit sitting behind a gray desk wearing a gray suit with a pair of notable silver cuff links of diapered cherubim called him by name and invited him to sit down on the chair in front of the desk.

“So, Jefferey, you clicked the link and now you’re here. Nice outfit, by the way, it suits you!” said the executive “We offer you the opportunity to rewind your life to any point you like. It could be a few days or a couple of decades. Are you interested?”

Jefferey had read fiction stories about this sort of thing. They often ended with the antagonist getting a devil’s bargain as they suffered the whims of the authors who wrote them. “Um, I don’t know. I would need more information before I make up my mind” said a cautious Jefferey.

“I suppose you’d be right to approach this deal cautiously,” responded the executive. “We’re prepared to give you a sample of any age you’d like to try before you commit if you like. The first taste is always free!” said the executive with a hint of smugness to his voice.

“What’s the catch? Do I have to give up my soul or some other valuable thing?” asked Jefferey as he wracked his brain looking for gotchas with the deal.

“No catch. No soul or valuable thing is necessary. Depending on how far back you rewind, the only thing you’ll lose is the material things that you accumulated past that rewind point as that would introduce a paradox. You get to keep your experiences unless you don’t want them, in which case we can wipe your mind back to the point you choose to go back to.” explained the executive.

“Just think, you have the chance to go back to anywhere in your past life and use your experience to change the outcome! What could be better than that?” asked the executive.

While Jefferey mulled the prospect over in his mind, the executive patiently waited while he thought about it.

Finally, Jefferey decided to give the trial offer a go. What could he lose?


Jeffery chose to revisit his first-ever date with Amanda Watkins. He was 12 years old and too scared to even kiss the girl. She had been around the block and a few gossipers said that the 13-year-old Amanda was loose as a goose and had a bit of a wild, partying streak.

That hadn’t happened with him. He suggested that they go bowling, rolled a few games with the evening ending in disappointment as the girl had waited for his signal to go a bit further all night and not receiving it, went home with Jefferey feeling a bit down over not being more assertive.

Boop! He was getting ready for his date and 12 years old with a few fine stray pubic hairs beginning to sprout from his gawky body in various places. He decided to not use the Aqua Velva this time as he noticed that she didn’t seem to like it. He did use the Right Guard, however, as he remembered sweating profusely from all the excitement of being with a girl and being so nervous that night.

Walking over to Amanda’s house, he decided to go to a movie with her instead and informed her of his changed plans for the evening. She immediately liked the idea and the possibility of doing a little heavy petting as well. Of course, she didn’t tell him that. “Let him figure it out,” she thought.

The two went to a movie that Jefferey wouldn’t remember anything about, (including the title!), later on in his life. It had started with hand-holding, moved to a casual embrace, and proceeded to first, second, and almost third base before she called the game off due to “rain” and asked to leave.

Jefferey was greatly saddened. He thought that he’d blown it by being too aggressive. When she invited him into her house and announced that her parents were out for the evening, then asked if he’d like to continue their baseball game in her room. Jefferey was ecstatic at the prospect!

They resumed their game with the first and second bases loaded as she guided Jefferey down to the third base. Jeffery was doing so well, that she wondered if he’d done this sort of thing before. He reassured her that she was his first and that she had been so nice that he felt that it was somehow right that they got as far as they did.

She quickly pulled off his pants and lay back on the bed inviting him to get in that home run if he wanted to.

Jefferey became a man that night.


Boop! He was back in the gray office wearing his soggy and uncomfortable ABDL outfit. He remembered the girl with fondness and then severe distaste.

“FU^&! Why didn’t you tell me she had VD and was revenging on every boy she could get her hands on? I would’ve been severely damaged for life had her parents not found out and her clinic informing a long list of boys that they were in dire need of penicillin shots!” shouted an angry Jefferey.

“You didn’t ask.” said the executive with a devilish smirk. “I suppose you’re soured on the offer, then?”

“Not entirely. But I think I see that there are hidden gotchas in your arrangement. I need more time to think about it and I need to get out of this outfit before I get a rash” said a sober Jefferey.

“Well, okay. When you’re ready, just click the link and we’ll discuss it further” said the executive as the office faded out of existence and Jefferey found himself back in his bedroom.

“I’m definitely developing a rash” he muttered as he stripped off his ABDL outfit and threw away the soggy diaper.


After much consideration, thinking, and diaper filling coupled with his dead-end job and the drudgery it entailed. Jefferey made up his mind to take the offer. Of course, he could have just re-trained and changed jobs to something he liked, but that would be too easy.

He clicked the link and eventually ended in the gray office seated in front of the executive. “Welcome back, Jefferey! I see that your taste in clothing has improved a bit since our last meeting” remarked the executive as he complimented Jefferey’s suit and tie combo.

“When in your life would you like to rewind to? Remember, this time it’s for keeps!”

“After much thought, I’ve decided to start from day one,” said Jefferey. Wearing diapers, being cared for, and not having any worries or cares for a while appealed to the world-weary side of him.

The executive was taken aback by this, he shrugged his shoulders and Jeremy disappeared leaving his fine clothing behind. “At last,” said the executive “I get a proper set of clothing for my wardrobe!”


Jefferey woke up. It was hard to open his eyes in the bright light of the delivery room, and everything was a blur. His eyesight wouldn’t get much better until his pupils developed in the next few weeks. His eyes burned with the mild silver nitrate wash that the delivery room crew had put in his eyes to prevent infection.

The too-tight diaper that the nurse had sadistically put on him chafed against the cauterized stub of his umbilical cord. He felt the intense cold of the room before they swaddled him in a delivery cloth and put him on his exhausted, sweaty mother’s breast. She hugged him with a smile and he was able to make out some features on her face.

Over the next year, Jefferey would experience vaccination shots, the croup, and a case of oral thrush. Why his parents decided on circumcision was beyond him and it was a very painful couple of weeks that he let them know of his displeasure at such a barbaric procedure.

His mother decided that cloth diapers were the way to go at four months but missed that part on the hippy website that said the diapers would have to be changed more often and that bleaching them was a no-no. It took several cases of diaper rash before a clinician clued her into some of the glossed-over aspects of using “greener” baby products.

Pneumonia at age 2 nearly wiped little Jefferey out. A fall down the stairs didn’t break any bones but left a painful bruise that hurt to sit on while it healed.

By age 3, his mother insisted that he be 100 percent potty-trained. This didn’t go well, as he wasn’t ready physically and sometimes out of spite would leave little “presents” behind the couch when he got the chance.

By age 5, he was wearing diapers to school. His pediatric doctor decided that his bladder muscles hadn’t been fully developed and wanted to give him more time.

At age 7, his dad left his sharp-tongued mother for a younger woman. This hadn’t happened in his previous life. He wondered what had changed.

At age 12, his family’s financial situation prevented him from getting any special classes that would develop his potential as an above-average child. To top it off, the public school he attended decided that all children were equal and that all children would advance at the same pace. This bored the hell out of him as the slower students usually took most of the class time to understand simple concepts that he understood immediately.

Age 14, still in diapers as his bladder muscles had atrophied due to sickness, Jefferey began to wonder if he wasn’t cursed.

Age 18, He had the grades despite the crappy school system to go to a better college, but not the funds. All the scholarships were either given to butt-kissers, or the less deserving. He chose the community college route for the first few years and would follow up with a degree at University provided he was able to sock enough money away.

At age 24, He got his master’s in a field that he liked early via CLEP exams. His finances weren’t nearly as bad as the other adults his age who grabbed up ridiculously large loans and took pottery classes while getting worthless degrees.


Jefferey came home from the lab, he puzzled a few of the equations that were giving the team troubles as they were solved. Nothing that couldn't be handled. Grabbing a beer and going to his bedroom, he pulled off his pants and got a diaper ready. He still needed them 24/7 due to his incontinence, and the appeal that they had in his previous life wasn’t there. They were just his underwear, after all.

He fired up his computer, took a swig from his beer bottle, and the screen lit up with a URL on his desktop that said “Click me!” It wouldn’t go away even after a fresh reload of the OS, so he muttered "Fu&* it!" under his breath and clicked it.

He appeared in the gray office of the executive who was wearing the suit that Jefferey had worn in his past life. “Jefferey! How’s it going? This is just a check-up to see if you’re satisfied with your offer, so I won’t take too much of your time” said the executive, all businesslike.

Jefferey thought about it and said “You know what? I wouldn’t have it any other way, thank you very much!”

The executive looked a little saddened, but shrugged his shoulders and said “You’re sure that you’re happy with your life now? Maybe just a little tweak to smooth things over? What do you say?”

Jefferey looked the executive in the eye and said “Judging by all the trials and tribulations that I went through in my second life, I’m quite satisfied. May I go now?”

(What he hadn’t said was that if his second life had more painful things in it than his first, his third would probably be a disaster.)

The executive smiled a sincere smile and wished him well.

Jefferey reappeared in his second life, already in progress.




End Chapter 1

You bet your life!

by: username | Complete Story | Last updated Apr 21, 2021


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