🎯 Where Should I Start?
All Book Series by Jess Winters
The Brat's Breeding Gap Year
Latest in the series · book 21 of 21 · published 2023
Chiseled CEO’s Little Girl
Latest in the series · book 15 of 15 · published 2025
Biker Daddy’s Beauty Across the Street
Latest in the series · book 40 of 40 · published 2023
My Fiance's Mafia StepDaddy Wants Me
Latest in the series · book 5 of 5 · published 2023
Billionaire's Second Chance Seduction
Latest in the series · book 10 of 10 · published 2024
Billionaire's Professorial Whispers
Series opener · book 1 of 5 · published 2024
Mountain Man's Academic Romance
Latest in the series · book 5 of 5 · published 2024
His Submissive Secret Little
Latest in the series · book 5 of 5 · published 2022
Forbidden Road Trip with Hubby's StepDaddy
Latest in the series · book 50 of 50 · published 2024
Foreman Daddy and Coffee Girl Little
Latest in the series · book 6 of 6 · published 2022
The Mafia Daddy's Dangerous Dilemma
Latest in the series · book 40 of 40 · published 2024
Mountain Man's Passionate Night
Latest in the series · book 10 of 10 · published 2024
Brother's Best Friend Seeks Nanny’s Lullaby
Series opener · book 1 of 10 · published 2025
Irresistible Billionaire’s Hired Nanny
Series opener · book 1 of 20 · published 2025
Observant Boxer's Hired Nanny
Latest in the series · book 20 of 20 · published 2026
The Sheriff Daddy's Petty Criminal Little
Series opener · book 1 of 6 · published 2023
Returning to My Sheriff Daddy
Latest in the series · book 6 of 6 · published 2023
Daddy Wants His Little Beauty Pleased
Latest in the series · book 35 of 35 · published 2022
Riding into a Midnight Encounter
Latest in the series · book 10 of 10 · published 2025
The Rancher and the Plus-Sized Cowgirl Little
Series opener · book 1 of 5 · published 2023
Under the Texas Sun with Daddy
Latest in the series · book 5 of 5 · published 2023
Rough Rides for Forbidden Love
Latest in the series · book 10 of 10 · published 2025
Relentless Tracker's Seductive Little
Latest in the series · book 10 of 10 · published 2022
Dominant Alpha's Best Friend's Temptations
Series opener · book 1 of 5 · published 2024
Mountain Man's Alpha Obsession
Latest in the series · book 5 of 5 · published 2024
Halloween with Sheriff Daddy
Latest in the series · book 33 of 33 · published 2022
The Sheriff's Forbidden Romance
Latest in the series · book 5 of 5 · published 2023
Daddy’s Promiscuous Little
Latest in the series · book 10 of 10 · published 2022
Never Say No to Boyfriend's Daddy
Latest in the series · book 15 of 15 · published 2023
Ashley's Three Friends to Three Lovers
Series opener · book 1 of 5 · published 2023
Samantha and Three Single Dads
Latest in the series · book 5 of 5 · published 2023
The Grumpy Billionaire's One Night Stand
Series opener · book 1 of 10 · published 2023
The Grumpy Billionaire's New Nanny
Latest in the series · book 10 of 10 · published 2023
Bound to His Reckless Heart
Latest in the series · book 20 of 20 · published 2026
Please Me Daddies Series Collection : Books 1-5
Latest in the series · book 3 of 3 · published 2021
? Frequently Asked Questions
Who is Jess Winters?
Jess Winters has 508 books catalogued in this guide spanning 2018–2026, across 35 named series.
Which Jess Winters series should I start with?
The best place to start is the Please Me Daddies series, the earliest of Jess Winters's multi-book series: it opens with Daddy's Frightened Little (2021) and runs to 35 books across 2021–2022, ending with Daddy Wants His Little Beauty Pleased (2022). Jess Winters's other series stand alone, so they can be read in any order.
How many books has Jess Winters written?
Jess Winters has 508 books catalogued in this guide, published between 2018 and 2026. 494 of them belong to 35 named series — the largest being the Her Taboo Older Man Age Gap Romance series with 50 books — and 14 are standalone titles, collections or anthologies.
In what order should Jess Winters's series be read?
Read each series in publication order — the numbered entries in each series follow the year each book first appeared. Jess Winters's series do not depend on one another, so they can be started in any order; by start date they are MC Protective Alpha (2020, 2 books), Please Me Daddies (2021–2022, 35 books) and Sheriff Daddies Little Girl (2021–2022, 33 books), plus 32 more.
How are Jess Winters's books organised into series?
This guide splits Jess Winters's 508 books into 35 named series and 14 titles that stand alone or appear only in collections: Her Taboo Older Man Age Gap Romance (50 books, 2022–2024); Diablo Ridge Motorcycle Daddies (40 books, 2022–2023); Mafia Daddies Ruthless Possession (40 books, 2022–2024); Please Me Daddies (35 books, 2021–2022); Sheriff Daddies Little Girl (33 books, 2021–2022), plus 30 further series.