Jack's Descent

by: AbolethLasher | Complete Story | Last updated Nov 2, 2021

Lauren was 19 when she first met the 43 year old Jack. She was always the younger one in the relationship, but soon she'll know what it's like to be the older partner.

Chapter 1
Full Story

Chapter Description: Lauren is tired of the big age gap between her and her lover.

Lauren had been wary of the age gap between her and Jack at first.

She had been 19, just out of a massage boot camp and trying to establish herself professionally when she had met the charming older man. Okay, he wasn’t *that* old, but a divorced guy in his early 40’s with a teenage daughter had not been Lauren’s first choice of a romantic partner.

It hadn’t started romantic at all, really.

They had met at a hot springs, and discovered they shared a number of interests. Jack was a wealthy, established lawyer and when he learned that Lauren was currently crashing on a friend’s couch and looking for a place to live, he offered to rent a spare bedroom in his now empty house. His ex-wife had primary custody of his daughter, after all, so he was all alone.

They had just been roommates at first. Well, landlord and tenant, but it never felt that way. Jack was sweet and funny and kind, and they started hanging out all the time.

However, both of them maintained that everything was strictly platonic.

After all, Jack was dating a woman his own age when they met, and Lauren was married to her work. It was hard getting a massage business up and running with little starting capital! She started small, with a portable set up doing house calls, but she dreamed of having a physical building with an atmosphere and clients she could have more control over.

However, the woman Jack was dating realized before he did that he was in love with Lauren. The three of them had watched a few TV shows together, and done a few group dinners and it was just so obvious. Jack’s girlfriend waited three patient months for him to come to that realization himself and break up with her.

When Jack had approached Lauren about the topic of dating, Lauren had been fairly resistant at first. She had to admit she did like the handsome older man, and had occasionally fantasized about him once or twice while in her bedroom alone. But there were two things standing in the way: first, of course, was her fledgling business, and second was the little fact that she was a virgin and had never really dated anyone. She had been a late bloomer, and though at 19 she was hot enough to be an Instagram influencer, she still felt like the ugly duckling she had been in high school.

Jack was very understanding, and gave her space, while starting to support her in small ways. Lauren was resistant at first - she was an independent woman and didn’t want somebody else’s charity, but her business had its high and low points, and in the low points she couldn’t say no to help with paying for gas, or waiving rent here and there.

Eventually, Lauren realized she could deny her own feelings no longer, and she finally said yes to Jack’s proposition. She quickly “moved in” to his house and stopped being a tenant altogether. They started renting the spare room to a friend, and things between Lauren and Jack blossomed.

Five years had passed since then, and everything was going wonderfully. Lauren had achieved her dream of getting a massage parlor of her own, while Jack had made partner at his law firm and was making more than enough money to give the two of them a very comfortable life together. He had been very wise in saving and investing his money, and could retire any time he wanted to - even his ex-wife and daughter were taken care of at this point. They weren’t even renting the spare room anymore.

Jack’s friends had been resistant to Lauren at first, insisting that he couldn’t date a girl that was only a few years older than his daughter, but once they had seen how sweet she was (possibly the nicest person in their group!) they had warmed up to her.

Lauren just had one misgiving. She was 24 and Jack was 47 and somehow the difference in their life experiences could never fully disappear into the background.

Jack was committed to her, and had supported her in starting up her business, but he seemed reluctant to marry again. His last relationship had gone up in flames, and so while he was happy to tie their lives together in other ways, and assured her that he was in the relationship for the long haul, he still wouldn’t pop the question.

Time started to become more and more important to Lauren. She became convinced that if he had met her when he was younger, if they had been closer in age, everything would have turned out different.

She also started to fear mortality more and more. It became a morbid obsession of hers that Jack was probably going to predecease her by 20 years. Then she’d be all alone. She hated that she was going to have fewer years than she would have liked with him.

So she started seeing if there was anything to do about time.

As a masseuse, a lot of her friends were involved in more mythical practices like reiki and acupuncture, so she asked around if anybody knew if there was anything they could do to make a person younger. The initial answers weren’t very reassuring. No, they said, aging is something we just have to accept - better health and natural longevity are possible, but nothing can turn back the clock.

But then one of her “witchy” patrons heard about her plight, and told her to come to her house for a special brew. Lauren had been nervous going to the old town home at the appointed hour. Something about the place just gave her the willies. She knocked on the door, which had probably once been blue, but now had whitish blue paint and was peeling in places.

No answer.

Lauren knocked again.

The old woman who had come to Lauren so many times for relief from her back pain opened the door. Lauren was surprised to see her dressed in a robe and a pointed hat. Lauren had formed a casual patron-client relationship with her, and didn’t know how she acted outside of their time together.

“Welcome,” the old woman said with a toothy smile. “Please come in! Can I get you any tea?”

Lauren walked into the house, which seemed to be a shrine to old taxidermy and abstract paintings. Something about the paintings unnerved her, as if they weren’t quite of this Earth, and every so often she imagined that one of the taxidermy pieces seemed to move when she looked away and looked back.

“So, a solution to old age is it, dearie?” the old woman said, chuckling a bit. “I’ve enjoyed aging gracefully myself, but I could see why you would want to preserve such beauty.”

Lauren smiled ruefully. “It’s not for me. It’s for my husband - he’s about twenty years older than me, and I can’t stop cursing the fact that we won’t have more time together.”

The old woman nodded. “Well, either way. Madame Zara has just the thing.” She pulled out a tiny bottle with a fluorescent green liquid inside. “Each drop of this dissolved in a drink will regress a person three years. I’d recommend getting a photo album or something put together - memories that aren’t reinforced soon after regression will disappear entirely.”

Lauren gulped. She hadn’t considered anything like that. “What about other people? Will they notice anything?”

Madame Zara shook her head. “The magic will take care of the people around him. As far as they will know, he will always have been the age he appears to be. Any contradictions will be smoothed over by their own minds filling in the blanks. And don’t worry about legal documents either, it is a very clever spell.”

Lauren nodded. “Alright, thank you Madame Zara. What do you want for this?”

The old woman shook her head. “It is my pleasure to grant the wishes of mere mortals. I only hope that this ends up being everything you want it to be.”

Lauren smiled and said goodbye, with the vial held firmly in her hand.

* * *

Lauren did the math, and knew she wanted to put 8 drops into Jack’s drink. That would make him 23 - just one year younger than her, and they would be able to enjoy a long, happy life together.

She decided to surprise him early on a Sunday morning with breakfast in bed. She layed out the plate and put the 8 drops into his morning coffee. Then she brought it up to him, along with the photo album she had printed out.

“What’s all this?” he said blearily, waking up to his beautiful girlfriend holding a tray.

“Breakfast in bed!” she said cheerily.

“What’s the occasion?” he said.

“Oh, I just wanted to do something nice for you, just because,” she said.

He smiled at her as she layed the tray down on his lap. She gave him a quick peck on the cheek, and watched eagerly as he eat.

“You’re making me a bit nervous hovering over me like that,” he said. “Why don’t you lie down with me, and we can watch the morning news together?”

Lauren got into bed, and cuddled up to Jack. She constantly glanced sideways to see his changes. After he had taken a few sips of the coffee, the changes started.

Jack was in good health at 47, but he still had hints of greying in his hair, and his face had the early signs of wrinking. As Lauren watched, his hair was the first thing to change. His hair became its original black, and it became thicker and more luscious. Then she noticed his face becoming more youthful.

He seemed to be in his 30’s now, and Lauren was not paying any attention to the news on in the background.

Jack looked confused at the screen. “Since when was Biden president?”

Lauren looked at him. “Since January of this year,” she said.

“Oh right,” Jack nodded uncertainly. “How could I forget?”

He continued to eat his breakfast, and grow younger. Soon he was in his late 20’s and he looked at Lauren confused.

“Woah, who are you?” he asked looking around at unfamiliar surroundings. “Where’s Stephanie?”

Stephanie had been his first wife, and it stung to hear him say those words. Lauren plopped the photo album in front of him, and tried to put on a brave face. If this went wrong, her whole plan was doomed.

“I’m Lauren, remember?” she said. “We’ve been through a lot together. See, this album?”

Jack flipped through the album as he finished off his coffee, and his unease and confusion seemed to lessen as he flipped through the pages. When he had finished, he smiled at Lauren and put his arms around her.

“I’m so sorry, Lauren!” he said. “I don’t know why I said a silly thing like that. Of course I remember you, my love!”

Lauren smiled. Everything had gone according to plan. Jack looked like he had in pictures she had seen of him at 23. He was so handsome, Lauren felt herself falling for him all over again.

“Well, thank you for breakfast in bed, Lauren,” he said. “I’ve got to go to law school now, I’ve got a lot of classes this early in the morning.”

Lauren looked at him. “Uh, you’re not a student anymore, honey. You’ve made partner. You’re a big shot lawyer now - that’s why we’ve got such a nice house.”

Jack nodded. “Er, right, uh, of course. How could I have forgotten? Well, in any case, I’ve got a law office to go to.”

Lauren kissed him on the lips. “Go get ‘em tiger,” she winked.

Jack looked rather flustered as he got up. Lauren thought it was cute. In his 40’s he had already basically seen and done everything when it came to romance, but Lauren knew from his stories that 23 year old Jack was less experienced. He had had a few girlfriends in high school and undergrad, but law school had taken up so much of his time he hadn’t really had time for girls. He was reacting like a young man who hadn’t touched a girl in a few years, instead of an established middle aged man who had been once divorced and had since been in a committed relationship for five years.

Jack got dressed, though something about his suit seemed to not quite fit him. Perhaps it was just the sense that he wasn’t effortlessly comfortable in it, having worn one for decades at this point.

At the law office, Jack felt out of his depth. He could almost force himself to remember all of his accumulated knowledge of the last 20 years, but a big part of him felt like he was still in law school and had never even set foot in a courtroom. He found himself delegating even more than usual, even for important cases, and in partner meetings he mostly just let other people do the talking, instead of taking charge himself.

For their part, his coworkers didn’t seem to notice anything strange about a 23-year-old being partner at a law firm. Even Jack himself didn’t really “notice” his own youth as something strange. His underlings did seem to talk down to him more, and ignore him more than usual, but if he tried to take charge they tended to step back and let the “more experienced” man take the lead.

By the end of the day, Jack decided to put in his two weeks notice. He didn’t know what it was, but he had lost his mojo. He wasn’t the confident, experienced man he had been yesterday. He had already been considering retiring, but now his plans had accelerated.

Besides, he was 23 and had plenty of time to pivot to another line of work if he wanted. In the mean time, it would be nice to retire and spend more time with his beautiful girlfriend Lauren. In fact, he reasoned as he was driving home, maybe he could make Lauren his wife! That was perfect, he'd buy a ring before getting home, and pop the question in two weeks once his retirement was finalized. He knew that Lauren had wanted to get married, and he now saw no reason to delay anymore.

When Jack arrived back at the house, the two of them held each other as if they were going to fall off the world. They made out with increasing intensity, and soon the two of them were making their way to the bedroom.

Lauren could tell the difference in Jack’s lovemaking. The old Jack had been unquestionably in charge in the bedroom. He always took the lead, and guided the two of them to a wonderful resolution.

But 23-year-old Jack didn’t have so many feathers in his cap. He was still taking the lead, but there was hesitation. Uncertainty. As if he was still probing the limits, still trying to figure some things out.

Lauren also sensed a vitality in him that she hadn’t in a while, as he ripped off her skirt and top.

Before, their bedroom antics had been fun, romantic and sexy, but Jack being an older man had always meant that Lauren had always had more stamina in the bedroom. Now that they were about the same age, Lauren enjoyed Jack’s youthful energy.

Normally, Jack had a whole arsenal of techniques and toys to made up for his age and flagging stamina, but now it was just the two of them skin-on-skin and Jacks every touch was electric and sensual.

While they made out, he ran his hands over her entire body, spending extra time on her ass and tits. She moaned and started teasing him through his underwear.

Jack got on top, and started dry humping her, while giving her hickies on her neck.

Lauren couldn’t help but giggle. As a middle aged man, Jack had never given her hickies, considering them a thing that young lovers did, but it was endearing seeing him do something he used to consider a little childish and adolescent, and speaking of adolescent… Jack had never used dry humping as a form of foreplay.

In his 40’s Jack was already an accomplished “cunning linguist” and had usually started a session by getting Lauren worked up with a little tongue action. Sometimes that was all they did, and he had her squirming and orgasming again and again.

By comparison, the current Jack lacked such finesse. He was just artlessly, if enthusiastically humping her through his strained underwear.

And it was *so* hot. Having a younger, less experienced lover was doing wonders for Lauren.

In fact, in the heat of the moment, she wondered if she couldn’t make things even more exciting.

Jack was 23 right now, just one year younger than her. But even though the gap in their experience had narrowed, it wasn’t far off. At 24, she had 5 years of experience with sex and dating, while he had had girlfriends in high school and undergrad.

Jack’s eyes were filled with animalistic passion, as he pulled her soaked panties down and lowered his own underwear. He was about to enter her, when she put up a hand.

“Hey, Jack,” Lauren panted. “I think I’ve got a way to make this even hotter.”

Jack seemed almost unable to control himself, but he nodded and said. “Alright, what is it?”

“Put your clothes back on.”

Jack was very confused, and little frustrated. “I thought you said you were going to make things hotter,” he complained.

Lauren bit his ear. “Oh, it will, wait until you see what I’ve got planned for you!”

Jack shivered. He started to do as he was told. He was so worked up, he probably would have done anything she asked at this point.

Once he was fully dressed, Lauren told him to open his mouth and stick out his tongue.

Jack realized Lauren must have some drugs or something. He had never really done anything harder than marijuana, but he was game to try.

Lauren grabbed the vial from her dresser, and plopped a single drop on his tongue.

“Now, keep your eyes closed for a bit. I’m going to change outfits.”

Jack sat there and let the drugs (or whatever it was) wash over him. It felt so pleasant, but it soon left him sitting there, wondering why his eyes were closed. Why was he so worked up?

“No peeking!” he heard an unfamiliar female voice say.

After a few more minutes, he heard someone whisper. “Okay, you can open your eyes.”

Jack saw the most sexy girl he had ever seen standing before him, in a school girl costume fit for a stripper. Her short skirt and stockings were really doing something for him, and he felt his pants tighten.

“You like?” the girl said in a high, girlish voice.

He nodded.

“Do you ‘member me, Jackie poo?” she said in that same exaggerated voice, stretching the fabric of her shirt teasingly.

“Of course I remember you,” he lied.

“Well, why don’t we finish what we started then?” she purred.

Jack didn’t need to be told twice. He stood up, and was soon making out with the mysterious, sexy girl. As he kissed her, flashes of memory started to trickle in. Her name was… Lexi? No, Lori?

No, Lauren!

She was his… roommate? Tenant?

As he kissed her, he realized it didn’t matter. He was so worked up already, and he just wanted to fuck. He was probably at a frat party or something.

He pushed her onto the bed, and ripped her sexy school girl uniform off.

Lauren felt a bit disappointed. She had hoped that three years would be enough for her to take the lead, but as he snapped her bra and stockings and was pulling down her underwear and going straight for the prize, she realized his two years in college had been more than enough sex education to make him a confident lover. Twenty was still too old.

“Wait,” Lauren said.

Jack stopped, his cock mere millimetres away from her pussy. It took every ounce of self control for him to just keep himself locked there. He wanted her so bad.

“Close your eyes and open your mouth real quick,” Lauren said.

Jack looked disappointed, but did what she asked. He felt a single drop, plop, land on his tongue. He felt someone shifting beneath him.

When he opened his eyes, he saw a hot girl in a school girl costume that looked like it had hastily been put back on underneath him, with the stockings uneven and the shirt ruffled. Her hair was slightly unkempt, as if she had been rolling around on the bed. He was alarmed to see his cock out, and quickly jumped off the bed and hastily pulled his pants up.

“Woah, what’s happening?” he said. “Who are you? Why was I naked?”

Lauren was so turned on by now, it was like a switch had flipped in her brain. The prospect of him forgetting because of the potion was so scary normally, but now it just made this encounter dangerous and sexy. Every minute she didn’t thoroughly remind him, the odds went up that he would forget all about her. That was a problem for future Lauren to worry about, though. Right now, she was going to fuck Jack’s teenaged brains out.

“I’m your girlfriend, Lauren,” she said teasingly. “Don’t you remember me?” She stood up, and walked enticingly towards him.

Lauren was amused to find that with her heels, she was looking down at 17-year old Jack. Gone was the fit, muscular man she had first met. Now he was a scrawny teenager, and she even saw a pimple or two. His pants even seemed to be threatening to fall down, and he was swimming in his shirt.

“L-Lauren?” he said uncertainly. “It does kind of ring a bell…”

“Why don’t I refresh your memory?” she whispered in his ear.

Jack shuddered. He had never had a girl so close to him.

“Have you ever seen a girl naked, Jack?” she asked.

Jack noticed as her hand brushed his arm, and felt his heart beating faster.

“N-no,” he said. “Not in person.”

“Would you like to?” she said.

Jack nodded.

Lauren took a step back.

“Well, I’m right here,” she said.

Jack just stood there, looking at her. Even being able to stare at her in that sexy costume was a dream come true. Her perfect breasts, her long, shapely legs and her ass were all so enticing, and they were right there in front of him, for him to take.

Jack raised a hand tentatively, and then lowered it.

He longed to see what was underneath her clothes, but was too nervous! He had had one girlfriend, but she had broken up with him after only a week. He was completely inexperienced.

“Why don’t I take the lead,” Lauren said. “Would you like that?”

Jack looked shyly at his feet, and nodded.

Lauren took a step towards him, grabbed his hand, and guided them under her white shirt.

Jack focused on the warmth, and the touch of her skin, the give of her breasts.

“Do you like that?” Lauren said.

Jack gave a slight smile, and nodded. “You’re not wearing a bra,” he said in surprise.

Lauren had a mischievous grin. “Now, take off my top,” she said.

Jack went wide-eyed. “Uh, um, okay.”

He started unbuttoning her top one by one - it wasn’t like before where he had practically ripped it off of her. He was respectful, hesitant, nervous.

Finally, her top was completely unbuttoned, and he got a good look at her bare breasts.

Jack’s arousal was through the roof. He was practically ready to cum right there. They were perky and perfect.

“Ah, ah, ah, don’t touch yourself just yet,” Lauren said softly, pushing his other hand away from his pants. “We’ve got a long way to go. Now take off my stockings.” She stepped out of her shoes, and pushed Jack to a kneeling position. She liked still having him beneath her.

Jack paused, before grabbing the top of her right stocking, and slowly pulling it down her leg. Lauren luxuriated in this feeling. The feeling of power over him.

She had always been the younger one, the ingenue. But now Jack was a trembling teenager, and she just loved the way he lapped up her every command. She was in control for the first time in her life, and she loved it.

“Now, the other one,” she said.

Jack rolled down her other stocking. She stood before him in just a mini skirt.

“Kiss my leg,” she said.

The young boy kissed her leg, just once at first, but after a moments hesitation, again and again.

“Now, get on the bed,” she commanded.

Jack looked longingly at her. She was drawing this out, teasing him, denying him release. But he was powerless before a woman so sexy.

Lauren got on top of Jack, and started making out with him. She helped him out of his slightly-too-large clothes and was rubbing her hands all over him. She was a masseuse, and her skillful ministrations were bringing Jack up to plateaus of arousal he didn’t think possible.

She straddled him, and pulled her panties down. She revealed Jack’s adolescent cock, pausing for a moment of amusement at the slight shrinkage he had endured, and started riding him. She was in the lead. She was in control, and Jack was happy to follow her anywhere.

The two of them moaned and moved together, as Lauren took Jack’s virginity. It was an incredible feeling, having a powerful woman on top of him, guiding him to manhood.

Because of his inexperience, it didn’t take long for him to come, but Lauren collapsed beside him, and rubbed her clit until she finished as well. Lauren had never experienced something quite so hot, and Jack certainly hadn’t either.

The two of them lay there panting, just existing as points of contact between two bodies that had been made one, cuddling and enjoying the afterglow.

After a few minutes, Jack finally felt the need to say something.

“That. was. amazing! But can you give me your name again, miss?”



End Chapter 1

Jack's Descent

by: AbolethLasher | Complete Story | Last updated Nov 2, 2021


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vended · Nov 3, 2021

A fun read! Is it finished?

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maniac78 · Nov 3, 2021

What a great story! Thank you!

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