Movies Like Deep Inside Kaitlyn Ashley

If you liked Deep Inside Kaitlyn Ashley (1996), a movie, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Yes, God, Yes (2020)
★ 6.3/10
Alice, a young innocent Catholic girl, is tempted into masturbating after an AOL chat suddenly turns sexual, however is conflicted as the act would be considered a sin.
2
sex, lies, and videotape (1989)
★ 7/10
Ann, a frustrated wife, enters into counseling due to a troubled marriage. Unbeknownst to her, her husband John has begun an affair with her sister. When John’s best friend Graham arrives, his penchant for interviewing…
3
Shadow in the Cloud (2021)
★ 5.8/10
A WWII pilot traveling with top secret documents on a B-17 Flying Fortress encounters an evil presence on board the flight.
4
Pink Floyd: The Wall (1982)
★ 8/10
A troubled rock star descends into madness in the midst of his physical and social isolation from everyone.
5
The Dreadful (2026)
★ 5.9/10
In medieval England, Anne and her domineering mother-in-law Morwen struggle to survive on the outskirts of society. But when a man from Anne's past returns from war, a curse begins to take shape through a mysterious…
6
Dante's Inferno: An Animated Epic (2010)
★ 7/10
Dante journeys through the nine circles of Hell -- limbo, lust, gluttony, greed, anger, heresy, violence, fraud and treachery -- in search of his true love, Beatrice. An animated version of the video game of the same…
7
I Spit on Your Grave 2 (2013)
★ 6.3/10
Broke, and in desperate need to update her portfolio, New York City model Katie calls a number from a tear-off flyer offering free photos. But this innocent attempt quickly turns into an unthinkable kidnapping…
8
Beyond the Valley of the Dolls (1970)
★ 6.1/10
An all-girl rock band moves to Hollywood in the hope of achieving success, only to fall into a whirlpool of wickedness and decadence.
9
Fairy Tales (1978)
★ 6/10
On his twenty-first birthday, the Prince goes on a quest that takes him across the land searching for the one woman that gets him sexually excited, Princess Sleeping Beauty.
10
Girl in the Bunker (2018)
★ 7.1/10
When Elizabeth is abducted by a fugitive sexual predator, she realizes she must take matters into her own hands and plot her escape. Based on a true story.
11
The Moment (2026)
★ 6.3/10
A rising pop sensation navigates fame and industry pressures while preparing for her arena tour debut, revealing the transformation of underground culture into mainstream success.
12
The Seasoning House (2012)
★ 6.3/10
The Seasoning House - where young girls are prostituted to the military. An orphaned deaf mute is enslaved to care for them. She moves between the walls and crawlspaces, planning her escape. Planning her ingenious and…
13
Selena Gomez: My Mind & Me (2022)
★ 8.4/10
After years in the limelight, Selena Gomez achieves unimaginable stardom. But just as she reaches a new peak, an unexpected turn pulls her into darkness. This uniquely raw and intimate documentary spans her six-year…
14
Lovelace (2013)
★ 6/10
Story of Linda Lovelace, who is used and abused by the porn industry at the behest of her coercive husband, before taking control of her life.
15
In the Lost Lands (2025)
★ 6.3/10
A queen sends the powerful and feared sorceress Gray Alys to the ghostly wilderness of the Lost Lands in search of a magical power, where she and her guide, the drifter Boyce, must outwit and outfight both man and demon.
16
The Girl Who Escaped: The Kara Robinson Story (2023)
★ 7.1/10
Based on a true story. 15-year-old Kara Robinson was kidnapped, assaulted and held captive for 18 hours. With her survival instincts kicking in, she plots a daring escape from the serial killer and leads police to his…
17
Private Parts (1997)
★ 6.5/10
The life and career of shock-jock superstar Howard Stern is recounted from his humble beginnings to his view from the top. Possessing a desire to be an on-air personality since childhood, Stern meanders through the…
18
Cobain: Montage of Heck (2015)
★ 7.6/10
Hailed as one of the most innovative and intimate documentaries of all time, experience Kurt Cobain like never before in the only ever fully authorized portrait of the famed music icon. Academy Award nominated…
19
Michael Jackson: Dangerous - The Short Films (1993)
★ 8.2/10
Michael Jackson's Dangerous album once again rocketed the global superstar to mega-platinum success! "Dangerous - The Short Films" captures the visual and musical highlights of his most recent string of hit singles. As…
20
Pitfall (2025)
★ 6.2/10
After a young man is separated from his friends in the woods, he falls into a ten-foot deep pit of spikes, impaling him through his leg and leaving him trapped. He quickly learns that his fall was not an accident.