When You Least Expect It - BabyAnna_03 - Wattpad

When You Least Expect It

Reads 29,926
Votes 829
Parts 12
Time 2h 3m

Reads 29,926
Votes 829
Parts 12
Time 2h 3m

agegap agere ageregression babygirl bossxemployee caregiver caregivers cg gxg headspace lgbt little littlegirl littlespace mama mommies mommy non-sexual nonsexual paci pacifier polyamory regression teacherxstudent wlw

Lily Wilson is in her early 20s. she's a college student who happens to live alone. She's also a little. 

one day after her friend insisted that she meet his friends. He takes her to his workplace which is a restroom/bar. 
after she's been welcomed by his coworkers/friends, they bump into his boss.



Vanessa Cooper is in her mid 30s. she's a businesswoman and owner of the restaurant/bar that Lily's friend works at. she's married to Elizabeth Cooper who is in her early 40s. they're caregivers who have been looking for a little for years. and when they meet Lily they both fall in love with her.All Rights Reserved

agegap agere ageregression babygirl bossxemployee caregiver caregivers cg gxg headspace lgbt little littlegirl littlespace mama mommies mommy non-sexual nonsexual paci pacifier polyamory regression teacherxstudent wlw

Table of contents

12 parts

Sign up to add When You Least Expect It to your library and receive updates

or

Content Guidelines

You may also like

TOUCH | A.R by hotcamaless

This is an AGE REGRESSION STORY COMPLETELY NONSEXUAL |. | When will I feel this As vivid as it truly is? Fall in love in a single touch And fall apart when it hurts too much |. | TRIGGER WARNING ⚠️ -mentions of abuse, violence, and guns. --------------------- In which a small named Willa lives on the streets, but when a certain group of people run into her and try to help her, they not only find out her traumatic past, but protect her with all they have. But who is to say the girls have a job they never want her to know. When they find her, it's just the beginning.

Teachers Pet || Joshler by x-PrettySleeper-x

Tyler has never had it easy, he's always had to fight to get what he wants...and he's always been alone; especially after the only person he depended on walked out- leaving him to fend for himself from such a young age. But- who would have thought being kicked out and sent to Ohio at 17 (by your own mother) would end up being so rewarding? (In the end) Regresser!Tyler Daddy!Josh Little!Brendon Daddy!Dallon Regression!Awsten Daddy!Geoff • COMPLETED ~ enjoy (: • Warning! This is not ddlb! Please keep my book away from the ddlb community as Tylers smallerheadspace and Josh's daddyheadspace is NOT a kink. I'd appreciate if you understood and did not sexualise the regression or add it to ANY kink lists because it is NOT kink.

The teachers baby by Yakuza_Lover2

SFW only story, so for all my littles don't worry you won't find any smut stuff in here, and content warnings trauma stuff. DO NOT ADD TO LISTS WITH NSFW ✨Also✨ highly important these chapters are a bit short, hopefully they'll be more words and longer stories I just don't want to bore anyone with long pages. Yes I have labeled this as romance I didn't know what to label it but it is SFW

She's different by CSEdward

Lily blue is very shy she doesn't like attention at all on her she is used to being in the background she don't like people looking at her since she is a big girl she has enough problems without people talking about her she works for a devil of a women as her assistant doing everything she needs an more !!! Lily cannot afford to quit she needs the money for her mothers hospital bills Lily mets her bosses brother an his business partner an they instantly take a liking to her but she tries to avoid them at all costs what will happen when they get a taste of her Sam Lupo an Nick Costa are have been together since college they are 28 now they are just more businesses partners they are a couple they love each other but they also miss having a women too they have tried to find a woman to add with them but they haven't found the one yet most women only want is their money an status they just about give up until they meet her she is so different from the other women an they love it A/N this story has a lot of sexual things in it if you don't like That then don't read it also this story has very mature things as well that can be unsettling to some people please do not read if you cannot Handle that also my story is my own. All characters are fictional. (©). "All Rights Reserved".

Good Little Life by cutelittlebean1

So this is my first story and it is about a girl who is 16 years old and her name is Anne. She has had a hard life with her parents always fighting leading to divorce and taking it out on her. Also at school she has a tough time because she's on the shy side and she gets bullied for it. She's also an age regressor but luckily she keeps that part of her life a secret. Andy is 18 and his life is pretty good his parents love him and so does his little sister. He's pretty popular at school too and kind to everyone. He's also a caregiver looking for a little girl to take care of. He sees a girl getting picked on and decides to help. What will happen when Anne and Andy meet? Keep reading to find out :)

✄𝐀 𝐋𝐢𝐭𝐭𝐥𝐞 𝐋𝐮𝐜𝐤--- Klance Little Space AU by Silkystars_

TW! Abuse, SH, SA mention, ED, sexual intimacy, age regression, panic attacks, depression, adult breastfeeding, and swearing **NON SEXUAL AGE REGRESSION** do NOT sexualize age regression in this story, it purely for a comfort and healing process. At no point will it be sexual. Lance never thought he could get this lucky. After living his whole life in a warehouse, accepting his fate that he'd never be free and die in the very spot he laid, what felt like a answered prayer appeared. Keith Kogane. Lance is finally given a second chance at life and Keith is more than ready to give the world to him. A chance to fully restart at life. But when Lance gets a little too comfortable, a new chapter begins and he finds a way to heal. Or: after Lance being locked away in a sex trafficking warehouse all his life, Keith comes to his rescue and while in healing find a new mechanism to cope, age regression.

Connected Hearts (GxG×G×G) by lynne_love_laugh420

Twyla Brooklyn is a 23 year old collage student majoring in the arts. She is desperately trying to outrun her home life and just take everything one day at a time. Struggling with PTSD, depression, chronic anxiety, and a side of her she is ashamed of. But little does she know she doesn't have to be. Carson Stone, Juniper Herring, and Bellamy Rameriz are 26-27 year olds who have been in a relationship of their own for 3 years now. Starting as just Cason and Bellamy when they were just teenagers, turned into a beautiful relationship with June (Juniper) and getting her more into their lifestyle. Twyla finds herself intertwined with the three women. Realizing that the once cruel world she viewed can hold some truly kindhearted and beautiful people. Ones that love her and make her feel at peace with herself. DISCLAIMER - This is a story where the main character deals with age-regression and uses it as a coping mechanism. - The main character struggles with a lot of mental health problems, and could be triggering for anyone reading this story. - THERE IS BDSM AS WELL. THE THREE OTHER MAINS DO NOT PARTICIPATE IN THEIR BDSM WHILE TWYLA IS IN LITTLESPACE. - THESE ARE ALL CONSENTING ADULTS. If you find anything about this to be offensive or you do not find this is the story for you, then I don't recommend it. Thank you.

Evening Romance by JeniRaeD

Austin and Vanessa have been together for 6 years, since college, Vanessa is 25 and Austin is 28, Austin surprises Vanessa with a 14 night, 15 day Caribbean cruise, Vanessa and her friends believe this is when he finally decides to pop the question. Vanessa is surprised when her best friends decide to surprise her and join her on the cruise and hope to be there when Austin gives her a ring. All of her friends are married or about to get married, she's the last of her closest friends to get married. Vanessa really wants to get married and to start a family. What will she do when she finds out the reason for the cruise? Will he pop the question or is there something else in store? Will she meet someone else and fall in love? contains sexual content and strong language as well as cheating... Credit for cover made by: https://selfpubbookcovers.com/SFcovers

Learning How to Bend by micamoney

Liliana "Lily" Hamill is just your average working woman. 5'5" with wavy brown hair the color of milk chocolate and blue eyes, she's never been described by anyone as "a catch." She's pretty enough, what with her athletic frame and well-proportioned face. She rises every day, runs almost every morning, and gets ready for work just like many twenty-something-year-olds in the United States. She's been working mostly in the marketing department at Andino Incorporated since she graduated from a college in Texas at twenty-one, and she's lived in New York City for the past two. She doesn't think she's anyone special. But she is, because Lily has been blind since birth, although her disability has never held her back. That burden has fallen on her insecurities. Now, though, she's attempting to face her fears. Her closest childhood friend, Joseph Montran, has invited her to a company social event, and Lily grudgingly has agreed to go. All she knows is that it's informal, that she and her guide dog, Chelise, can mostly hang out with Joe and his wife, Katherine, if that's what Lily wants, and that she shouldn't be afraid to "act natural." What she doesn't know is that social event will change her life forever. //// I KEEP EDITING AS I'M WRITING. I'm sorry to anyone who gets updates for old parts to which I make minor grammatical changes. Don't kill me. c:

You may also like

Slide 1 of 9

TOUCH | A.R cover

Teachers Pet || Joshler cover

The teachers baby cover

She's different cover

Good Little Life cover

✄𝐀 𝐋𝐢𝐭𝐭𝐥𝐞 𝐋𝐮𝐜𝐤--- Klance Little Space AU cover

Connected Hearts (GxG×G×G) cover

Evening Romance cover

Learning How to Bend cover

TOUCH | A.R

This is an AGE REGRESSION STORY COMPLETELY NONSEXUAL |. | When will I feel this As vivid as it truly is? Fall in love in a single touch And fall apart when it hurts too much |. | TRIGGER WARNING ⚠️ -mentions of abuse, violence, and guns. --------------------- In which a small named Willa lives on the streets, but when a certain group of people run into her and try to help her, they not only find out her traumatic past, but protect her with all they have. But who is to say the girls have a job they never want her to know. When they find her, it's just the beginning.