Story cover for When You Least Expect It by BabyAnna_03
When You Least Expect It
  • WpView
    Reads 101,915
  • WpVote
    Votes 2,318
  • WpPart
    Parts 22
  • WpHistory
    Time 3 hours, 28 minutes
  • WpView
    Reads 101,915
  • WpVote
    Votes 2,318
  • WpPart
    Parts 22
  • WpHistory
    Time 3 hours, 28 minutes
Ongoing, First published Aug 19, 2022
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.
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A Littles Journey (age regression)

48 parts Ongoing

In a world where being a little is normal. in fact little and caregivers are the norm, as well as owners and pets, masters and subs. Once a certain age, you are offered to go to school to learn and be in a good environment for your assigned role. Of course which is determined by a test you take once you pass or are the age of 18. Little Bell is sent to the biggest littles academy in the country by her loving parents after her testing. As nervous as she is, she tries her best to make a good first impression. Which works good enough to make a good little friend with his caregiver... But also good enough to run into two scary looking yet kind and loving caregivers ~~~~~~~~ (No sexual active or SMUT between the main littles and caregivers! This is a SFW age regression, with some small talks of smut and flirting💞) #1 caregiver 03/02/25 #1 caregivers 03/02/2025 #2 academy 02/01/25 #1 agere 02/28/25 #1 in bottles 02/27/25 #1 in cribs 04/5/25