Evelyn’s Regression

Hey guys, I’m working on role reversal stories. I have created a Patreon where this story is already finished, but I will be posting more chapters in here. What other scenarios you’d like to see? Let me know so that I can add them to the list. At the moment I’m working on two other stories: One about an older brother turned into a baby and the other about a father. My Patreon is https://www.patreon.com/LittlerWriter?fan_landing=true
If you join, I will be adding new stories weekly and you can even tell me if you want me to continue with Evelyn’s regression or you prefer something new!


Hailee heard her mother crying through the baby monitor, and as she was already used to it, she left her desk and went straight to the nursery. When she opened the door she was hit by the smell of a very stinky diaper, and, knowing how bizarre the situation was, she stood there for a minute, with her eyes scanning the woman sitting in her pink crib.

Her mother, who had been an elegant and beautiful woman just three months prior, was looking uncomfortable and with her eyes watery. Hailee knew she wanted a change, as if the smell wasn’t telling enough, but her mother’s eyes were saying something more. She could talk, if she needed something she could say it, but that’s not how babies work, is it?

Hailee got closer to her, ready to be the grown up of the house.

Chapter One

Evelyn and Hailee couldn’t be more different from one another. The mother, Evelyn, was an English teacher at the local college. She was chubby, but at almost 40 years old and 5’7 feet, she was still looking young and attractive. Though, all eyes were on her daughter, who at 6’0 and only 19 years old was a towering woman with a stunning body. Hailee was into fitness, and her body was a testament to it, but she was more than just her look. She worked from home as a manager for a small but successful company, though her mother knew nothing about and she like to keep it that way.

They had what could only be described as a difficult relationship, though you wouldn’t know by just looking at them interact in public. If there was something Hailee hated the most was public scenes, especially from teenagers or young adults, her peers. So, whenever her mother would piss her off, she would wait until they were home and try to talk things with her. Though, Evelyn wasn’t really interested in having calm or polite conversations, which made Hailee questioned who was the actual adult in the house.

Now, you might be wondering what happened to make Evelyn end up in diapers at the mercy of her daughter?

Well, it all began three months ago, after Hailee turned 19, just a couple of months before Evelyn would turn 40.

Hailee woke up that morning, ready to hit the gym as she did every morning, it was not even 6 a.m, but that was her routine. She was already used to the fact that her mother would oversleep, whether it was constant drinking, the waking up late, or the toxic friends she would hang out with, Hailee knew that her mother was who she was at this point of life, and there wasn’t much she could do about it.

So, she picked up her bag and left home as she did every week day.

Almost two hours later, Evelyn woke up in her room almost crying her eyes out. She didn’t want to move, she knew what had happened. What had been happening for almost a month now, and she only wanted to be swallowed by the earth instead dealing with it. But, she had to get ready soon, and she couldn’t be late anymore, or things would get worse.

She stood up, doing her best to ignore the smell and the cold touch of her PJs, and went straight to shower. It was lucky that she had her own bathroom attached to her room, or else she would risk being discovered by her daughter. However, when she entered her shower, she noticed she had run out of shampoo, again. With no time to get a new one, she left her room, completely naked and went to her daughter’s bathroom, taking Hailee’s shampoo and returning to her own bathroom. She turned the water one and let her worries be washed away by the stream of hot water.

Evelyn finished showering, got ready, opened a window in her room, and went straight to work. She would deal with her wet bed when she returned because she didn’t have the time nor the mental energy to deal with it right now.

Just a couple of minutes after Evelyn left for work, Hailee arrived home in need of a shower. She went to her bathroom, hoping for a nice hot shower, but there was no shampoo. It couldn’t run out, she just got a new one, which meant only one thing, her mother had forgotten to get her her own and had come for hers.

Hailee sighed, but knowing Evelyn should already be gone to work, she went to her mother’s bathroom to reclaim her precious shampoo. All the way thinking how irresponsible her mother was, but that stopped when she opened the door to Evelyn’s room.

The smell hit her like a punch in the face, a combination of ammonia and sweat, and something more.

She had never babysit or been that close to a baby before, but the smell was too obvious to ignore. She went to her mother’s bed to find it completely soaked, and in her mother’s bathroom, she found her soaked clothes. There was no doubt about what had happened, and her mother, responsible as she was, didn’t even clean after herself.

Had her mother drink too much that sh peed herself? Why would she not even remove the sheets to wash them? Or do something with her soaked clothes? Seriously, some times she was worst that a baby.

Hailee sighed, not knowing what to do, and left her mother’s room. She needed to do something, but what? Then, it hit her. She had an idea, she needed a plan, but that was her specialty

Chapter Two

At work, Evelyn couldn’t think of anything but the last month and the many times she had almost peed herself while dictating her class. It was one thing to wet the bed, but an entire different issue to wet herself in front of her students, many of whom were the same age as her daughter.

“Okay, so…” said Evelyn, clutching her tights, “That’s everything for today. Remember that the test will cover the entire second chapter of the book,” she kept saying as most of her students left.
Well, all of them but one.

Her star student, and a very handsome one to say the least, Michael. His dark hair and dark eyes were complement but his manly voice and, obviously, a hot body.

“Amazing class,” he said, smiling at her “You have so much knowledge of the Beat Generation. Who’s your favorite?”

“I would have to say Kerouac, and it is a cliché, but his writing is so…,” she stopped, her bladder was screaming now, “Honest,” she finished, picking her things, “I’m afraid I have to go now, Michael, have some stuff to do.”

“Sure, I’ll see you around”

Even if Evelyn enjoyed chatting with him as much as possible, she couldn’t help to notice that she was starting to drip a little into her panties. So, she said nothing else and left straight to the bathroom.

“Fuck,” she muttered as she released her pee, noticing that she had indeed wet herself a bit. Not enough to be noticeable, but enough to make it uncomfortable to move around.

Thank god, I’m wearing black pants and panties, she thought, trying to dry as much of her underwear with toilet paper as she could. Finally, when she felt it was good enough, she left the restroom and headed to her car. With every step she could feel her wet panties getting colder and colder, and more uncomfortable. She only hoped no one would be able to notice.

Before she could reach her car, someone stopped her.

“My, my, if it isn’t the hottest MILF in the world,” Evelyn heard and turned to see her friend, Brenda.

She was slightly shorter than Evelyn herself, but her body was amazing, especially for a fifty year old teacher. Though, with all her drinking, her face was looking a bit older than her body, something Evelyn feared it would happen to her. But, nowadays, drinking was the only thing that kept her sane.

“How was your class? Oh, don’t tell me. Boring? But what about that exquisite specimen you teach?”

“Shhh,” said Evelyn, blushing slowly as she noticed Michael also entering his car not too far from them. He was looking so hot, and she felt herself getting wet, though she was glad this time it was because of how horny she felt every time she saw her student.

“Don’t worry. He didn’t hear. Though, if he did, I bet he would be interested”

“How are you a teacher in here?” Asked Evelyn, chuckling, hoping Michael would actually try to do her.

Brenda did something with her mouth that answered Evelyn’s question.

“Everything is settled, we are going to Vegas the weekend of your birthday.,” said Brande getting closer to her friend, “We’ll get fucked all the way to your 41st birthday’

Evelyn only smiled, feeling her bladder getting full again. Fuck, she though, I just went to the bathroom.

“That sounds good, though I haven’t told Hailee yet”

“I mean, she can cum with us. If you know what…”

“Stop. I know what you mean, and yuk”

“Just kidding. Anyway, I still have one more class, so I’ll leave you to it,” said Brenda, spanking Evelyn’s butt. The impact made Evelyn let out some drops of pee in her panties.

Brenda stopped, feeling her hand a bit wet. But that couldn’t be unless…unless Evelyn had peed herself. No, that’s not possible, not even her would do that unless she had drank more than usual.
“Is everything okay?” Asked Evelyn, shyly.

“Yeah, yeah, I’ll talk to you later. Love” said Brenda, leaving the parking lot.

Evelyn got into her car, decided to hold her pee until she got home. Just a twenty minutes drive, that shouldn’t be too hard. Should it?

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